KR100355131B1 - 7-Glycosyloxybenzopyran derivative and antiallergic agent containing the derivative as active ingredient - Google Patents

Abstract

The present invention relates to 7-glycosyloxybenzopyran derivatives of the general formula (I) and physiologically acceptable salts thereof.

In the above formula,

R ₁ is a hydrogen atom, acyl group, alkyl group, cycloalkyl group, alkenyl group or aralkyl group,

R ₂ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group,

R ₃ is a glycosyl group wherein the hydroxyl group is protected or unprotected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups.

Description

7-Glycosyloxybenzopyran derivative and antiallergic agent containing the derivative as active ingredient

The present invention relates to a 7-glycosyloxy benzopyran derivative obtained by glycosylating a 7-position hydroxyl group of a benzopyran derivative with a hexose derivative. This compound or physiologically acceptable salt thereof is useful as an antiallergic agent.

Benzopyran derivatives as aglycone residues of the 7-glycosyloxybenzopyran derivatives of the present invention are described, for example, in EP 0 598 117 by inventors of the present invention, and similar benzopyrans For derivatives, see Donald T. Witiak, J. Med. Chem., Vol. 31, pp. 1473-1445, 1988 and US Pat. No. 4,845,121, but not 3- or 4-glycosyloxybenzopyran derivatives thereof as 7-position glycosides. In addition, the anti-allergic activity of the 7-glycosyloxybenzopyran derivatives of the present invention and their physiologically acceptable salts is not known.

Since anti-allergic agents available on the market are not satisfactory in terms of efficacy, safety and bioavailability, studies to develop anti-allergic agents have been conducted in depth. For example, tranilast (common name), a common anti-allergic agent, is administered at high doses to treat allergic diseases despite the low acute toxicity value (LD ₅₀ ) of mice (780 mg / kg). Since there is a need for this, the use of efficacious and toxic amounts of access, i.e. the narrow safety range, raises a problem that needs attention. In addition, disodium cromoglicate (common name), a well-known anti-asthma agent, whose clinical efficacy has been confirmed, is satisfactory in toxicity, but is used by spray inhalation because the absorption rate of the gastrointestinal tract is extremely poor. do. In addition, these known anti-allergic agents are not effective against delayed allergy but are effective against immediate allergy. Chronic conditions of allergic diseases, including asthma and atopic dermatitis, are serious problems, and delayed allergy is deeply involved in the development of chronic conditions. As a result, agents effective for both immediate and delayed allergies are preferred as antiallergic agents. As is well known, steroids are effective for both immediate and delayed allergies, but cause extremely serious side effects.

As discussed above, most of the anti-allergic agents reported so far have insufficient effects on delayed allergy and thus cannot show sufficient therapeutic effect, and thus have many disadvantages. Due to this poor method of administration is limited. As a result, great attention has been paid to the development of drugs that can be used for oral administration, have low toxicity, and are effective in both immediate and delayed allergies.

The inventors of the present invention have provided, according to European Patent Publication No. 0 598 117, an antiallergic agent comprising a benzopyran utobody and the active ingredient thereof. This time, in view of the problems associated with the prior art as mentioned above, the present invention seeks to provide new substances that are more useful as pharmaceuticals and anti-allergic agents with low toxicity and excellent effectiveness.

In order to provide more useful compounds as medicaments, the inventors of the present invention have disclosed various glycosylated compounds by glycosylating the 7-position hydroxyl groups of the benzopyran derivatives described in EP 0 598 117 with hexose derivatives. It was synthesized and tested for its antiallergic activity and safety. As a result, the present inventors found that the 7-glycosyloxybenzopyran derivative of the following general formula (I) can exhibit very excellent antiallergic activity with low toxicity. The present invention has been made based on this finding. Accordingly, the present invention provides the following 7-glycosyloxybenzopyran derivatives of general formula (1), physiologically acceptable salts thereof, and 7-glycosyloxybenzopyran derivatives of general formula (I) or physiologically acceptable thereof Antiallergic agents comprising salts as active ingredients

It is about mechanism.

In the above formula,

R ₁ is a hydrogen atom, acyl group, alkyl group, cycloalkyl group, alkenyl group or aralkyl group,

R ₂ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group,

R ₃ is a glycosyl group wherein the hydroxyl group is protected or unprotected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups.

First, the 7-glycosyloxybenzopyran derivative of general formula (I) is demonstrated.

In general formula (I) of this invention, R <_1> is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group, or an aralkyl group.

Examples of acyl groups include alkanoyl groups (e.g. acetyl, propionyl, butyryl, isobutyryl, etc.), aroyl groups, e.g. benzoyl groups (e.g. p-meth), which may have a benzoyl group or a substituent group. Oxybenzoyl, p-methylbenzoyl, p-chlorobenzoyl or p-nitrobenzoyl) and the like and acyl groups such as alkoxycarbonyl groups such as methoxycarbonyl or ethoxycarbonyl, and the like. Of these, alkanoyl groups are preferred, and acetyl groups are particularly preferred.

Examples of alkyl groups include straight or branched chain acyclic alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-methylpentyl, hexyl, octyl, decyl , Dodecyl, etc.), and are preferably an alkyl group having 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms.

Examples of cycloalkyl groups include linear or branched cycloalkyl groups such as unsubstituted cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl and cyclooctyl, and cycloalkyl groups substituted by alkyl groups such as 4-methylcyclohexyl and dimethylcyclohexyl, etc.), of which cycloalkyl groups having 5 to 8 carbon atoms in the ring and side chains are preferred, and 4-methylcyclohexyl is particularly preferred.

Examples of alkenyl groups include straight or branched chain alkenyl groups (e.g., vinyl, propenyl, pentenyl, hexenyl, heptenyl, octenyl, nonyl, decenyl, 3-methyl-2-butenyl, geranyl, etc.) And an alkenyl group having 2 to 10 carbon atoms, more preferably 6 to 10 carbon atoms.

Examples of aralkyl groups can be used as hydroxyl group protecting groups such as benzyl groups or benzyl groups which may have substituent groups (eg p-methoxybenzyl, p-methylbenzyl, p-chlorobenzyl or p-nitrobenzyl) and the like. Benzyl groups, including unsubstituted groups, are particularly preferred.

In general formula (I) of the present invention, R ₂ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group.

Examples of alkyl groups include straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-methylpentyl, hexyl, octyl, decyl, dodec Yarn, etc.), and is preferably an alkyl group having 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms.

Examples of cycloalkyl groups include unsubstituted cycloalkyl groups (eg cyclopropyl, cyclopentyl, cyclohexyl and cyclooctyl) and cycloalkyl groups substituted with alkyl groups (eg 4-methylcyclohexyl and dimethylcyclohexyl); Preference is given to cycloalkyls comprising the same straight or branched cycloalkyl groups, of which cycloalkyls having from 5 to 8 carbon atoms in the ring and side chains are particularly preferred, 4-methylcyclohexyl.

Examples of alkenyl groups include straight or branched chain alkenyl groups (e.g., vinyl, propenyl, pentenyl, hexenyl, heptenyl, octenyl, nonyl, decenyl, 3-methyl-2-butenyl, geranyl, etc.) And an alkenyl group having 2 to 10 carbon atoms, more preferably 6 to 10 carbon atoms.

Examples of aralkyl groups are used as hydroxyl group protecting groups such as benzyl groups (eg p-methoxybenzyl, p-methylbenzyl, p-chlorobenzyl or p-nitrobelzyl) which may have a benzyl group or a substituent group. Especially preferred are unsubstituted benzyl groups.

The glycosyl group of R ₃ in formula (I) is a glucosyl, mannosyl and galactosyl group in which all or part of the hydroxyl group, which is related to the binding of the glycosyl group, may or may not be protected by a protecting group. Is selected from. In general, sugars are known to have D and L stereoisomers and these are also included in the present invention. Hexose derivatives used as materials of glycosyl groups are glucose, mannose and galactose, in which all or part of the hydroxyl groups may or may not be protected by a protecting group, of which unprotected glycosyl groups are preferred. The 7-glycosyloxybenzopyran derivative, which is the compound of the present invention, is a compound in which any one of these hexose derivatives is bonded at the 7 position of the benzopyran derivative through a glycoside bond. Such glycoside bonds may include α- and β -bonds, both of which are included in the 7-glycosyloxybenzopyran derivatives of the present invention.

For glycosyl groups protected with protecting groups, preferred examples of protecting groups include groups commonly used as saccharide protecting groups such as acyl, aralkyl and the like. In such cases, examples of acyl groups include alkanoyl groups (e.g. acetyl, propionyl, butyryl, isobutyryl, etc.), aroyl groups (e.g. benzoyl groups (e.g. p- Methoxybenzoyl, p-methylbenzoyl, p-chlorobenzoyl or p-nitrobenzoyl), and the like and alkoxycarbonyl groups such as methoxycarbonyl or ethoxycarbonyl, and the like. Particularly preferred.

Examples of aralkyl groups include benzyl groups, such as p-methoxybenzyl, p-methylbenzyl, p-chlorobenzyl or p-nitrobenzyl, which may have benzyl groups or substituent groups.

Preferred protecting groups are benzyl groups and acetyl groups, of which acetyl groups are particularly preferred.

Depending on the type of substituent groups of R ₁ and R ₂ , galactose may be used as the most preferred glycosyl group, followed by glucose and mannose in order. Also, unprotected glycosyl groups are preferred over protected glycosyl groups.

In view of anti-allergic activity, preferred examples of the 7-glycosyloxybenzopyran derivatives of the invention are those wherein R ₁ is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group, and R ₂ is a hydrogen atom, an alkyl group, a cyclo An alkyl group or an alkenyl group, wherein R ₃ is a glucosyl, mannosyl or galactosyl group, more preferred examples where R ₁ is an alkyl group, a cycloalkyl group or an alkenyl group, and R ₂ is hydrogen An atom, wherein R ₃ is a glucosyl, mannosyl, or galactosyl group; most preferred examples are compounds in which R ₁ is an alkyl group, R ₂ is a hydrogen atom, R ₃ is a glucosyl group, R ₁ is a cycloalkyl group, R ₂ is a hydrogen atom, R ₃ is a glucosyl group, R ₁ is an alkenyl group, R ₂ is a hydrogen atom, R ₃ is a glucosyl group, R ₁ is Alkyl group, R ₂ is number A small atom, R ₃ is a galactosyl group, R ₁ is a cycloalkyl group, R ₂ is a hydrogen atom, R ₃ is a galactosyl group, and R ₁ is an alkenyl group, R ₂ Is a hydrogen atom and R ₃ is a galactosyl group.

The preparation method of the 7-glycosyloxybenzopyran derivative of the present invention is summarized below.

7-glycosyloxybenzopyran derivatives of the general formula (I) of the present invention can be prepared, for example, by a method according to the following reaction scheme:

In the above formula,

R ₁ , R ₂ and R ₃ are as defined above,

R ₄ is an acyl group or an aralkyl group which is a protecting group of the hydroxyl group of the hexose derivative,

X is a halogen atom.

In the first step, the 7-hydroxybenzopyran derivative (1) and the hexose halide derivative of the general formula (2) described in the preceding application by the inventor of the present invention (E0 0 598 117) Glycosylated. Hexose halide derivatives can be prepared according to known methods, respectively. See L. J. Haynes and F. H. Newth, Adv. Carbohydr. Chem. 10, 207 (1955); W. Korytnyk and J. A. Mills, J. Chem. Soc., 1959, 636.

The preparation of the benzopyran derivative (1) used in the present invention as starting material is described in detail in EP 0 598 117. That is, this derivative can be prepared according to the following scheme.

First, the hydroxyl group of 2,4-dihydroxyacetophenone (a) is protected with benzyl group to give compound (b). The carbon atom of the compound thus obtained is then increased by the reaction of this compound with dimethyl carbonate to convert this compound into a ketoester compound (c), followed by reaction with benzoyl peroxide to give compound (d). In this step, the benzyl group used as the hydroxyl group protecting group is hydrocracked to remove the protecting group and then treated with acid to yield the benzoyloxy compound (e). The benzoyl oxy compound (e) thus obtained is then treated with a metal alkoxide in a nonaqueous system to remove the benzoyl group to obtain the benzopyran derivative (f).

The benzopyran derivative (1) in which R ₁ is an acyl group other than the benzoyl group is synthesized as follows. The 7-hydroxy compound is obtained by acylating the hydroxyl groups at the 3 and 7 positions of the benzopyran derivative (f) and then selectively removing the acyl groups at the 7 position.

A benzopyran derivative (1) in which the 4-position is substituted with an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group is synthesized as follows. The benzopyran derivative (f) obtained by protecting the hydroxyl groups at positions 3 and 7 is subjected to alkylation, cycloalkylation, alkenylation or aralkylation of the hydroxyl groups at position 4.

The benzopyran derivative (1) in which the 3-position is substituted with an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group (1) is synthesized by selectively removing the acyl group in the 3-position, followed by alkylation, cycloalkylation, alkenylation or aralkylation. . The benzopyran derivative (1) can be obtained by selectively introducing a substituent.

Using the benzopyran derivative (1) and hexose derivative (2) thus obtained, the hydroxyl group at the 7 position is glycosylated according to the known Koenigs-Knorr method. In such glycosylation, metal catalysts (eg silver salts, preferably silver oxide, silver carbonate, etc.) can be used in the known König-Nor method to promote the reaction.

In this reaction, an organic solvent is used as a reaction solvent. Preferred examples of the solvent include ether solvents (e.g. diethyl ether, tetrahydrofuran, dimethoxyethane, dioxane, etc.), amide solvents (e.g. dimethylformamide, dimethylacetamide, etc.) and nitrile solvents (e.g. acetonitrile, Propionitrile and the like). In general, the reaction can be carried out at -20 to 50 ° C, preferably 0 to 30 ° C for 1 to 30 hours. In this way, 7-glycosyloxybenzopyran derivatives of the general formula (3) are obtained.

When synthesizing a compound in which the hydroxyl group is not protected in the glycosyl group, the deprotection reaction is carried out by debenzylation or deacylation of the hexose moiety of the general formula (3) as a second step, which is a conventional method. Can be achieved. In other words, in the case of debenzylation, the reaction is carried out by hydrocracking using a metal catalyst under an atmosphere of hydrogen gas.

Examples of the metal catalyst include catalysts such as palladium, platinum, and the like, and the catalyst may be used in an amount of 1 to 10% by weight based on the weight of the compound of formula (3). The reaction in hydrogen gas can be carried out under pressurized conditions or under atmospheric pressure. The reaction can generally be carried out in a solvent. Preferred examples of the solvent include alcohol solvents (e.g. methanol, ethanol, propanol, butanol, etc.), ether solvents (e.g. diethyl ether, tetrahydrofuran, dioxane, etc.) and acetic acid ester solvents (e.g. methyl acetate, ethyl acetate, Propyl acetate and the like). The reaction can be carried out generally at a temperature of 10 to 50 ° C, preferably 0 to 30 ° C for 1 to 5 hours.

Deacylation also allows the compounds to be selected from hydroxides (e.g. sodium hydroxide, potassium hydroxide, lithium hydroxide, etc.) as bases and alcoholate bases (e.g. sodium methoxide, potassium methoxide, sodium ethoxide). , Potassium ethoxide, etc.).

Preferred examples of reaction solvents used in this reaction include lower alcohols (e.g. methanol, ethanol, propanol, etc.), ether solvents (e.g. diethyl ether, tetrahydrofuran, dimethoxyethane, dioxane, etc.) and amide solvents (e.g. : Dimethylformamide, dimethylacetamide, etc.). The reaction temperature is variable depending on the reaction reagent and solvent used, and is preferably in the range of -10 to 50 ° C, more preferably 0 to 30 ° C. The reaction time is generally 1 to 5 hours. The following compounds are examples of 7-glycosyloxybenzopyran derivatives of the present invention.

3,4-dihydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one

3-undecanyloxy-4-hydroxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-hydroxy-7- ( β -D-gluropyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzyloxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- (tetra--0-acetyl-β-D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- (tetra-0-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-hydroxy-7- (tetra-0-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzyloxy-4-hydroxy-7- (tet-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucofuranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-gluropyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzoperran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-gluropyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one.

3-acetoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-denzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O) -benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxy benzyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzyloxy-4-hydroxy-7- (α-D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-hydroxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-hydroxy-7- (tetra-O-acetyl-α-D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- (tetra-0-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy group-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-0-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-benzyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzyloxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-eulactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-eulactopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dihydroxy-7- (tetra-O-benloyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (detra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-hydroxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-methoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-ethoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-isopropoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-butoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hexyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-octyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-decanyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-Undecanyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-cyclohexyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (cis-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (trans-4-methylcyclohexyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (3-hexenyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-geranyloxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3,4-dibenzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3- (p-methoxybenzyloxy) -4-benzyloxy-7- (tetra-O-benzyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-methoxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-ethoxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-isopropoxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-butoxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-hexyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-octyloxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-decanyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-undecanyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-cyclohexyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (cis-4-methylcyclohexyloxy) -7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (trans-4-methylcyclohexyloxy) -7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (3-hexenyloxy) -7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-geranyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (p-methoxybenzyloxy) -7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-methoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-ethoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-isopropoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-decanyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-undecanyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-cyclohexyl-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (cis-4-methylcyclohexyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (trans-4-methylcyclohexyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-geranyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (p-methoxybenzyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-methoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-ethoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-isopropoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-butoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-1-one

3-benzoyloxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-octyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-decanyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-undecanyloxy-7 (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-geranyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-banzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4- (p-methoxybenzyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-methoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-ethoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-isopropoxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-octyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-geranyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-methoxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-ethoxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-isopropoxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-butoxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hexyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-octyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-decanyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-undecanyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

2-acetoxy-4- (3-hexenyloxy) -7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-geranyloxy-7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (p-methoxybenzyloxy) -7- (tetra-O-benzoyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-methoxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-ethoxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-isopropoxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-butoxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-hexyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-octyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-decanyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-undecanyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-cyclohexyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (cis-4-methylcyclohexyloxy) -7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (trans-4-methylcyclohexyloxy) -7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (3-hexenyloxy) -7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-geranyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (p-methoxybenzyloxy) -7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-methoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-ethoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-isopropoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-butoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hexyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-octyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-decanyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-undecanyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-cyclohexyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (cis-4-methylcyclohexyloxy) -7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (trans-4-methylcyclohexyloxy) -7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-geranyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (p-methoxybenzyloxy) -7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-methoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-L-benzopyran-2-one

3-benzoyloxy-4-ethoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-isopropoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-butoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hexyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-octyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-decanyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-undecanyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-geranyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4- (p-methoxybenzyloxy) -7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-methoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-ethoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-isopropoxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hexyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-octyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-geranyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-methoxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2E-1-benzopyran-2-one

3-acetoxy-4-ethoxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-isopropoxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-butoxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hexyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-octyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-decanyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-undecanyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (3-hexenyloxy) -7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-geranyloxy-7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (p-methoxybenzyloxy) -7- (tetra-O-benzoyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-methoxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-ethoxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-isopropoxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-butoxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-hexyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-octyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-decanyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-undecanyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-cyclohexyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (cis-4-methylcyclohexyloxy) -7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (trans-4-methylcyclohexyloxy) -7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (3-hexenyloxy) -7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-geranyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4-benzyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-hydroxy-4- (p-methoxybenzyloxy) -7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-methoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-ethoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-isopropoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-decanyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-undecanyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-cyclohexyloxy-7- (tetra-O-acetyl- β -D-galactopyranopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (cis-4-methylcyclohexyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (trans-4-methylcyclohexyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-geranyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (p-methoxybenzyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-methoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-ethoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-isopropoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-octyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-decanyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-undecanyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-geranyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-benzoyloxy-4- (p-methoxybenzyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-methoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-ethoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-isopropoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-octyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4- (3-hexenyloxy) -7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-propionyloxy-4-geranyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-methoxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-ethoxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-isopropoxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-butoxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-hexyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-octyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-decanyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-undecanyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (3-hexenyloxy) -7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4-geranyloxy-7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

3-acetoxy-4- (p-methoxybenzyloxy) -7- (tetra-O-benzoyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one

Physiologically acceptable salts of these compounds are also exemplified.

As used herein, the term “physiologically acceptable salts” means, for example, non-toxic alkali addition salts of the compounds mentioned above, including sodium salts, potassium salts, magnesium salts, calcium salts, ammonium Salts, non-toxic amine salts, and the like. Such physiologically acceptable salts can be prepared by known methods, and these are also included in the present invention.

The 7-glycosyloxybenzopyran derivatives of the present invention and physiologically acceptable salts thereof (hereinafter referred to as "compounds of the present invention") inhibit both immediate and delayed allergic reactions which will be described later in the Examples. It is useful as an antiallergic agent for the treatment or prevention of various allergic diseases because of its function.

As used herein, the term “allergic disease” means an allergic disease due to overactivity of biological immune mechanisms caused by exogenous or endogenous antigens, including immediate asthma, delayed asthma, bronchial asthma, childhood Asthma, atopic dermatitis, allergic dermatitis, gallitis, eczema, allergic conjunctivitis, allergic rhinitis, hyperthermia, food allergy, allergic gastroenteritis, allergic colitis, drug allergy, contact dermatitis, autoimmune disease Included.

Antiallergic agents comprising the compounds of the present invention as active ingredients may be administered orally or parenterally (eg, intravenous injection, subcutaneous injection, transdermal absorption, rectal administration, etc.). Such agents can be in various dosage forms depending on the purpose, for example tablets, capsules, granules, fine subtilaes, powders, troches, sublingual agents, suppositories, ointments, injections, emulsions, suspensions, It can manufacture with a medicinal syrup. Such formulations include pharmaceutically acceptable carriers commonly used in this type of formulation, such as excipients, binders, disintegrants, lubricants, preservatives, antioxidants, isotonic agents, buffers, coatings, sweeteners, solubilizers, It can be manufactured according to a known method using carriers, such as a base, a dispersing agent, a stabilizer, and a coloring agent.

Examples of such pharmaceutically acceptable carriers are listed below.

Firstly, excipients include starch and derivatives of starch (e.g. dextrin, carboxymethyl starch, etc.), cellulose and cellulose derivatives (e.g. methylcellulose, hydroxypropylmethylcellulose, etc.), sugars (e.g. lactose, sucrose, glucose, etc. ), Silicates and silicates (e.g. natural aluminum silicate, magnesium silicate, etc.), carbonates (e.g. calcium carbonate, magnesium carbonate, sodium bicarbonate, etc.), magnesium aluminum hydroxide, synthetic hydrotalcite, polyoxyethylene derivatives, glycerin monostea Latex, sorbitan monooleic acid and the like.

Examples of binders include starch and starch derivatives (e.g. alpha starch, dextrins, etc.), cellulose and cellulose derivatives (e.g. ethylcellulose, sodium carboxymethyl cellulose, hydroxypropylmethyl cellulose, etc.), gum arabic, tragant, gelatin, sugars (e.g. : Glucose, sucrose, etc.), ethanol, polyvinyl alcohol, etc. can be mentioned.

As disintegrants, starch and starch derivatives (e.g. carboxymethyl starch, hydroxypropyl starch, etc.), cellulose and cellulose derivatives (e.g. sodium carboxymethyl cellulose, crystalline cellulose, hydroxypropylmethyl cellulose, etc.), carbonates (e.g. calcium carbonate , Calcium hydrogen carbonate, etc.), tragant, gelatin, agar, and the like.

Lubricants include stearic acid, calcium stearate, magnesium stearate, talc, silicic acid and salts thereof (e.g. light silicate anhydride, natural aluminum silicate), titanium oxide, calcium hydrogen phosphate, anhydrous aluminum hydroxide gel, macrogol and the like.

Preservatives include p-hydroxybenzoate, sulfites (e.g. sodium sulfite, sodium pyrosulfite, etc.), phosphates (e.g. sodium phosphate, calcium polyphosphate, sodium polyphosphate, sodium metaphosphate, etc.), alcohols (e.g. chlorobutanol, Benzyl alcohol, etc.), benzalkonium chloride, benzetonium chloride, phenol, cresol, chlorocresol, dihydroacetic acid, sodium dihydroacetate, glycerin sorbic acid, sugar and the like.

Antioxidants include sulfites (e.g. sodium sulfite, sodium bisulfite, etc.), rongalite, erythorbic acid, L-ascorbic acid, cysteine, thioglycerol, butylhydroxyanisole, dibutylhydroxy toluene, propyl gallic acid, ascorbic acid Bill palmitate, dl- α -tocopherol, and the like.

Isotonic agents include sodium chloride, sodium nitrate, potassium nitrate, dextrin, glycerin, glucose and the like.

Buffers include sodium carbonate, hydrochloric acid, boric acid, phosphates such as sodium hydrogen phosphate.

Coating agents include cellulose derivatives (e.g. hydroxypropyl cellulose, cellulose acetate phthalate, hydroxypropylmethyl cellulose phthalate, etc.), shellac, polyvinylpyrrolidone, polyvinylpyridine (e.g. poly-2-vinylpyridine, poly-2) -Vinyl-5-ethyl pyridine and the like), polyvinylacetyl diethylamino acetate, polyvinyl alcohol phthalate, methacrylate, methacrylate copolymer and the like.

Sweetening agents include sugars (eg, glucose, sucrose, lactose, etc.), sodium saccharin, sugar alcohols and the like.

Solvents include ethylenediamine, nicotinamide, sodium saccharin, citric acid, citrate, sodium benzoate, soap, polyvinylpyrrolidone, polysorbate, sorbitan fatty acid esters, glycerin, propylene glycol, benzyl alcohol and the like.

Bases include fats (e.g. lard), vegetable oils (e.g. olive oil, sesame oil, etc.), animal oils, lanolin acid, petroleum, paraffin, waxes, resins, bentonite, glycerin, glycol oils, higher alcohols (e.g. stearyl alcohol , Cetanol).

Dispersants include gum arabic, tragant, cellulose derivatives (such as methyl cellulose), stearic acid polyesters, sorbitan sesquioleate, aluminum monostearate, sodium alginate, polysorbates, sorbitan fatty acid esters, and the like. have.

Finally, stabilizers include sulfites (eg sodium hydrogen sulfite), nitrogen, carbon dioxide and the like.

The content of the compounds of the present invention in these pharmaceutical preparations may vary depending on the formulation, but may preferably be contained at a concentration of 0.01 to 100% by weight.

The dosage of anti-allergic agents of the invention can vary widely depending on the individual mammal to be treated, including the human, mouse, rat, swine, etc., the severity of each disease, the judgment of the physician, and the like. In general, however, for oral administration, it can be administered at a dose of 0.01 to 200 mg, preferably 0.01 to 50 mg, more preferably 0.05 to 10 mg of active ingredient per kg of body weight per day, and for parenteral administration, 1 day It can be administered at a dose of 0.01 to 10 mg, preferably 0.5 to 5 mg of active ingredient per kg of body weight.

The following examples are intended to illustrate the compounds of the present invention and methods of preparing pharmaceutical compositions of these compounds, but these examples are intended to illustrate the invention and should not be considered as limiting the scope of the invention.

Reference Example 1

3-methoxy-4-benzyloxy-7-acetoxy-2H-1-benzopyran-2-one

Sodium carbonate under argon atmosphere in a mixture of 8.11 g (27.8 mmol) of 3-methoxy-4-hydroxy-7-acetoxy-2H-1-bencopyran-2-one and 5.71 g (33.4 mmol) of benzyl bromide in 50 ml of DMF. 4.61 g (33.4 mmol) is added and the mixture is stirred at 50 ° C. for 2 hours. The solid in the reaction mixture is filtered off, the filtrate is poured into 200 ml of water and extracted with 500 ml of benzene. After drying over magnesium sulfate, the organic layer is concentrated in vacuo to give an oily residue. The residue was purified by silica gel column chromatography (eluent: benzene / ethyl acetate = 7/3) to afford 3.50 g of the title compound (yield 33%).

¹ H-NMR (CDCl ₃ , δ -TMS): 7.67 (d, 1H, J = 8.8 Hz), 7.40 (m, 5H), 6.82 (d, 1H, J = 8.8 Hz), 6.78 (s, 1H) , 5.45 (s, 2H), 3.85 (s, 3H), 2.32 (s, 3H)

IR (KBr, cm ^-1 ): 1760, 1720, 1620, 1435, 1360, 1220

Elemental Analysis for C ₁₉ H ₁₆ O ₆

Calculated (%): C 67.05; H 4.75; O 28.20

Found (%): C = 67.15; H 4.63; O 28.22

Reference Example 2

3-methoxy-7-hydroxy-4-benzyloxy-2H-1-benzopyran-2-one

To a mixture of 3.64 g (10.7 mmol) of 3-methoxy-4-benzyloxy-7-acetoxy-2H-1-benzopyran-2-one in 50 ml of methanol was added 0.58 g (10.7 mmol) of sodium methoxide, The mixture is stirred at rt for 1 h. Then, 2.31 g of Amberlyst-15 (trade name: Organo Corp.) is added and the mixture is stirred at room temperature for 1 hour. The angler-15 is filtered off and the filtrate is concentrated under reduced pressure. The precipitate is obtained during concentration and filtered to give 2.59 g of the title compound (yield 77%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.30 (bs, 1H), 7.67 (d, 1H, J = 8.8 Hz), 7.40 (m, 5H), 6.72 (d, 1H, J = 8.8 Hz), 6.78 (s, 1H), 5.45 (s, 2H), 3.78 (s, 3H)

IR (KBr, cm ^-1 ): 3200, 1760, 1720, 1620, 1435, 1360, 1220

Elemental Analysis for C ₁₇ H ₁₄ O ₅

Calculated (%): C 68.45; H 4.73; O 26.82

Found (%): C 68.25; H 4.73; O 27.02

Reference Example 3

3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one

To a mixture of 17.31 g (51.79 ml) of 4-butoxy-3,7-diacetoxy-2H-1-benzopyran-2-one in 170 ml of methanol was added 2.66 g (49.20 mmol) of sodium methoxide and the reaction mixture was cooled to room temperature. Stir for 3 hours. Then 22.36 g of Amberlyst-15 is added and the mixture is stirred at room temperature for 1 hour. Amberlyst-15 is filtered off and the filtrate is concentrated under reduced pressure to afford the crystalline product. The product was reprecipitated with tetrahydrofuran and hexane to give 12.87 g of the title compound (yield 85%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.60 (s, 1H), 7.64 (d, 1H, J = 8.8 Hz), 6.87 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz) , 6.75 (d, 1H, J = 2.4 Hz), 4.42 (t, 2H, J = 6.21 Hz), 2.33 (s, 1.80-1.70 (m, 2H), 1.55-1.40 (m, 2H), 0.94 (t , 3H, J = 7.4 Hz)

IR (KBr, cm ^-1 ): 3200, 2950, 1760,1690, 1620, 1410, 1340

Elemental Analysis for C ₁₅ H ₁₆ O ₆

Calculated (%): C 61.64; H 5.52; O 32.84

Found (%): C 61.60; H 5.53: 0 32.87

Reference Example 4

3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one

According to Reference Example 3, 4-hexyloxy-3,7-diacetoxy-2H-1- instead of 4-butoxy-3,7-diacetoxy-2H-1-benzopyran-2-one 30.00 g (82.79 mmol) of benzopyran-2-one are used to give 22.01 g of the title compound (yield 83%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.63 (s, 1H), 7.63 (d, 1H, J = 8.8 Hz), 6.86 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz) , 6.74 (d, 1H, J = 2.4Hz), 4.41 (t, 2H, J = 6.2Hz), 2.32 (s, 3H) 180-1.70 (m, 2H), 1.50-1.25 (m, 4H), 0.87 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3200, 2930, 1760, 1690, 1620, 1410, 1340

Elemental Analysis for C ₁₇ H ₂₀ O ₆

Calculated (%): C 63.74; H 6.29; O 29.97

Found (%): C 63.73; H 6.26; O 29.98

Reference Example 5

3-acetoxy-4-octyloxy-7-hydroxy-2H-1-benzopyran-2-one

According to Reference Example 3, 4-octyloxy-3,7-diacetoxy-2H-1-benzo instead of 4-butoxy-3,7-diacetoxy-2H-1-benzopyran-2-one 30.00 g (76.84 mmol) of pyran-2-one give 23.19 g of the title compound (yield 87%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.62 (s, 1H), 7.63 (d, 1H, J = 8.8 Hz), 6.86 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz) , 6.74 (d, 1H, J = 2.4Hz), 4.46 (t, 2H, J = 6.4Hz), 2.32 (s, 3H), 1.80 to 1.65 (m, 2H), 1.50 to 1.10 (m, 6H), 0.85 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 3200, 2900, 1760, 1690, 1620, 1410, 1340

Elemental Analysis for C ₁₉ H ₂₄ O ₆

Calculated (%): C 65.50; H 6.94; O 27.55

Found (%): C 65.38; H 6.98; O 27.64

Example 1

3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (Compound 1)

1.53 g (5.12 mmol) of 3-methoxy-4-benzyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 4.21 g (10.23 mmol) of glucopyranosyl bromide are dissolved in 20 ml of acetonitrile under an argon atmosphere at room temperature. To this solution is added 1.19 g (5.12 mmol) of silver oxide (I) and 13.77 g of molecular sieve 4A (Merck), and the mixture is stirred at room temperature for 2 hours. After filtration, the filtrate is concentrated under reduced pressure to give an oily residue. The residue was purified by silica gel column chromatography (eluent: benzene / ethyl acetate = 2/1) to give 1.77 g of the title compound (1) (yield 55%).

¹ H-NMR (CDCl ₃ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.20-7.40 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.78 (s, 1H), 5.42 (s, 2H), 5.25 to 5.35 (m, 2H), 5.14 (t, 1H, J = 8.0 Hz), 4.93 (d, 1H, J = 8.0 Hz), 4.21 to 4.28 (m, 2H ), 3.82-3.85 (m, 1H), 3.78 (s, 3H), 2.02-2.22 (m, 12H)

IR (KBr, cm ^-1 ): 1750, 1620, 1435, 1360, 1240

Elemental Analysis for C ₃₁ H ₃₂ O ₁₄

Calculated (%): C 59.23; H 5.09; O 35.68

Found (%): C 59.40; H 4.95; O 35.65

Example 2

3-methoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (Compound 2)

2.19 g (3.48 g of 3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one in 20 ml of ethyl acetate under hydrogen atmosphere mmol) and 0.22 g of 10% palladium on activated carbon are stirred at room temperature for 2 hours. The catalyst is filtered off and the filtrate is evaporated to afford the crude product. After washing the crude product with diethyl ether, 1.59 g of the title compound (2) is obtained (yield 85%).

¹ H-NMR (CDCl ₃ , δ -TMS): 10.50 (bs, 1H), 7.70 (d, 1H, J = 8.8 Hz), 6.88 (d, 1H, J = 8.8 Hz), 6.78 (s, 1H) , 5.25 to 5.35 (m, 2H), 5.14 (t, 1H, J = 8.0 Hz), 4.93 (d, 1H, J = 8.0 Hz), 4.21 to 4.28 (m, 2H), 3.82 to 3.85 (m, 1H ), 3.78 (s, 3H), 2.02-2.22 (m, 12H)

IR (KBr, cm ^-1 ): 3250, 1750, 1620, 1435, 1360, 1240

Elemental Analysis for C ₂₄ H ₂₆ O ₁₄

Calculated (%): C 53.53; H 4.83; O 41.64

Found (%): C 53.40; H 4.90; O 41.70

Example 3

3-methoxy-4-hydroxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (Compound 3)

0.58 g (1.07 mmol) of 3-methoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one in 12 ml methanol under argon atmosphere 0.15 g of sodium methoxide was added to the mixture of N) at 5 ° C, followed by stirring at room temperature for 1 hour. 0.75 g of Amberlyst-15 is then added and the mixture is stirred at room temperature for 1 hour. Excess methanol is added to dissolve the precipitate produced during neutralization, then amberlist-15 is filtered off and the filtrate is concentrated in vacuo to give a precipitate. Filtration yields 0.31 g of the title compound (3) (yield 77%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J = 8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J = 8.4 Hz), 4.98 (bs, 4H), 4.83 (d, IH, J = 7.6 Hz), 3.85, (s, 3H), 3.65 (d, 1H, J = 7.6 Hz), 3.51 (d, 1H, J = 7.6 Hz), 3.41 (m, 1H), 3.31-3.20 (m, 3H)

IR (KBr, cm ^-1 ): 3350, 1660, 1630, 1580, 1270

Elemental Analysis for C ₁₆ H ₁₈ O ₁₀

Calculated (%): C 51.89; H 4.90; O 43.21

Found (%): C 51.52, H 4.85; O 43.63

Example 4

3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one (Compound 4)

According to Example 1, 2,3,4,6-tetra-O-acetyl- β -D-mannopira instead of 2,3,4,6-tetra-O-acetyl- α -D-glucopyranosyl bromide 4.21 g (10.23 mmol) of nosyl bromide are used to yield 1.88 g (58% yield) of the title compound (4).

¹ H-NMR (CDCl ₃ , δ -TMS): 7.67 (d, 1H, J = 8.4 Hz), 7.20-7.40 (m, 5H), 6.95 (s, 1H), 6.94 (d, 1H, J = 8 , Hz), 6.00 (s, 1H), 5.55 (m, 2H), 5.45 (s, 2H), 5.40 (m, 5H), 4.23 (m, 2H), 4.15 (s, 1H), 3.75 (s, 3H), 2.02 ~ 2.22 (m, 12H)

IR (KBr, cm-1): 1750, 1620, 1435, 1360, 1240

Elemental Analysis for C ₃₁ H ₃₂ O ₁₄

Calculated (%): C 59.23; H 5.09; O 35.68

Found (%): C 59.40; H 5.15; O 35.45

Example 5

3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1benzopyran-2-one (compound 5)

Carried out according to Example 1, 2,3,4,6-tetra -O- acetyl - α -D- glucopyranosyl bromide in place of the 2,3,4,6-tetra -O- acetyl - α -D- galacto 4.21 g (10.23 mmol) of pyranosyloxy bromide is used to obtain 1.82 g of the title compound (5) (yield 56%).

¹ H-NMR (CDCl ₃ , δ -TMS): 7.72 (d, 1H, J = 8.8 Hz), 7.20-7.40 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.78 (s, 1H), 6.01 (s, 1H), 5.55 (m, 2H), 5.45 (s, 2H), 5.40 (s, 1H), 5.16-5.25 (m, 1H), 4.10-4.20 (m, 2H), 3.90 (s, 3H), 2.02-2.22 (m, 12H)

IR (KBr, cm ^-1 ): 1750, 1620, 1435, 1360, 1240

Elemental Analysis for C ₃₁ H ₃₂ O ₁₄

Calculated (%): C 59.23; H 5.09; O 35.68

Found (%): C 59.42; H 5.15; O 35.43

Example 63-methoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one (Compound 6)

In accordance with example 2, 3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one instead of 3-methine 0.321 g of the title compound (6) is obtained using methoxy-4-benzyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one ( Yield 81%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J = 8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J = 8.4 Hz), 6.00 (s, 1H), 5.55 (m, 2H), 5.40 (m, 1H), 4.23 (m, 2H), 4.15 (s, 1H), 3.75 (s, 3H), 2.02-2.22 (m , 12H)

IR (KBr, cm ^-1 ): 3350, 1660, 1630, 1580, 1270

Elemental Analysis for C ₂₄ H ₂₆ O ₁₄

Calculated (%): C 53.53; H 4.83; O 41.64

Found (%): C 53.42; H 4.55; O 42.03

Example 7

3-methoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 7)

According to Example 2, 3-methoxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one instead of 3-methine 0.309 g of the title compound (7) is obtained using oxy-4-benzyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one. (Yield 78%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J = 8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J = 8.4 Hz), 4.85 (d, 1H, J = 7.6Hz), 3.85 (s, 3H), 3.65 (d, 1H, J = 7.6Hz), 3,51 (d, 1H, J = 7.6Hz), 3.41 ( m, 1H), 3.20-3.40 (m, 3H), 2.05-2.22 (m, 12H)

IR (KBr, cm ^-1 ): 3350, 1660, 1630, 1580, 1270

Elemental Analysis for C ₂₄ H ₂₆ O ₁₄

Calculated (%): C 53.53; H 4.83; O 41.64

Found (%): C 53.42; H 4.55; O 42.03

Example 8

3-methoxy-4-hydroxy-7- (α-D-mannopyranosyloxy) -2H-1-benzopyran-2-one (Compound 8)

In accordance with Example 3, 3-methoxy-4-hydroxy-7- (tetra-0-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one instead of 3-methine 0.310 g of the title compound (8) is obtained using methoxy-4-hydroxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one ( Yield 78%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J = 8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J = 8.4 Hz), 6.00 (s, 1H), 5.55 (m, 2H), 5.40 (m, 1H), 4.98 (bs, 4H), 4.23 (m, 2H), 4.15 (s, 1H), 3.75 (s, 3H )

IR (KBr, cm ^-1 ): 3350, 1660, 1630, 1580, 1270

Elemental Analysis for C ₁₆ H ₁₈ O ₁₀

Calculated (%): C 51.89; H 4.90; O 43.21

Found (%): C 51.52; H 4.85; O 43.63

Example 9

3-methoxy-4-hydroxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (Compound 9)

According to Example 3, 3-methoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one instead of 3-methine 0.295 g of the title compound (9) is obtained using methoxy-4-hydroxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one. (Yield 74%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 11.25 (bs, 1H), 7.67 (d, 1H, J = 8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J = 8.4 Hz), 5.00 (bs, 4H), 4.85 (d, 1H, J = 7.6 Hz), 3.85 (s, 3H), 3.65 (d, 1H, J = 7.6 Hz), 3.51 (d, 1H, J = 7.6 Hz), 3.41 (m, 1H), 3.20-3.40 (m, 3H)

IR (KBr, cm ^-1 ): 3350, 1660, 1630, 1580, 1270

Elemental Analysis for C ₁₆ H ₁₈ O ₁₀

Calculated (%): C 51.89; H 4.90: 0 43.21

Found (%): C 51.65; H 4.85; O 43.50

Example 10

3-acetoxy-4-benzyloxy-7- (tetra-O-benzyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (compound 10)

According to Example 1, 3-methoxy-4-benzyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 1.00 g (3.06 mmol) of 3-acetoxy-4-benzyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O- in place of glucopyranosyl bromide 2.70 g (4.43 mmol) of benzyl- α -D-glucopyranosyl bromide was used to obtain 1.52 g of the title compound (10) (yield 58%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.67 (d, 1H, J = 8.8 Hz), 7.15-7.60 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 5.42 (s, 2H), 5.25 to 5.35 (m, 2H), 5.20 (m, 8H), 5.14 (t, 1H, J = 8.0 Hz), 4.93 (d, 1H, J = 8.0 Hz ), 4.21-4.28 (m, 2H), 3.82-3.85 (m, 1H), 2.38 (s, 3H)

IR (KBr, cm ^-1 ): 1760, 1640, 1600, 1450, 1380

Elemental Analysis for C ₅₂ H ₄₈ O ₁₁

Calculated (%): C 73.58; H 5.66; O 20.76

Found (%): C 73.53; H 5.78; O 20.69

Example 11

3-acetoxy-4-hydroxy-7- ( β -D-glucopyranosiloxy) -2H-1-benzopyran-2-one (compound 11)

1.50 g (1.77 mmol) of 3-acetoxy-4-benzyloxy-7- (tetra-O-benzyloxy- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one under argon atmosphere Dissolve in 150 ml of tetrahydrofuran at room temperature and add 0.15 g of 10% palladium on activated carbon. After argon gas has been replaced with hydrogen gas, the reaction mixture is stirred at room temperature for 2 hours. The catalyst is filtered off and the filtrate is evaporated to yield crystalline product. After reprecipitation with tetrahydrofuran and hexane, 0.662 g of the title compound (11) was obtained (yield 94%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.5 (bs, 1H), 7.70 (d, 1H, J = 8.4 Hz), 6.70-6.90 (m, 2H), 5.80 (bs, 1H), 5.32 (d, 1H, J = 7.2 Hz), 5.19 (s, 1H), 5.02 (s, 1H), 4.50 (s, 1H), 3.10-3.70 (m, 6H), 2.33 (s, 3H)

IR (KBr, cm ^-1 ): 3400, 1780, 1670, 1610, 1580, 1270

Elemental Analysis for C ₁₇ H ₁₈ O ₁₁

Calculated (%): C 51.26; H 4.52; O 44.22

Found (%): C 51.27, H 4.51; O 44.22

Example 12

3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 12)

11.74 g (40.18 mmol) of 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 24.74 g (60.27 mmol) of galactopyranosyloxy bromide are dissolved in 360 ml of acetonitrile under an argon atmosphere at room temperature. 11.17 g (48.21 mmol) of silver oxide (I) and 106 g of molecular sieve 4A were added to the solution, and the mixture was stirred at room temperature for 4 hours. After filtration, the filtrate is concentrated under reduced pressure to give an oily residue. The residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 2/1) to give 13.00 g of the title compound (12) (yield 52%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.05 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 2.4Hz), 5.20 ~ 5.30 (m, 2H), 4.52 (t, 1H, J = 6.6Hz) , 4.46 (t, 2H, J = 6.0 Hz), 4.11 (d, 2H, J = 6.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H), 1.70 ~ 1.80 (m, 2H), 1.40 ~ 1.55 (m, 2H), 0.93 (t, 3H, J = 3.6Hz)

IR (KBr, cm ^-1 ): 2950, 1750, 1630, 1370, 1240

Elemental Analysis for C ₂₉ H ₃₄ O ₁₅

Calculated (%): C 55.95; H 5.50; O 38.55

Found (%): C 55.84; H 5.58; O 38.58

Example 13

3-acetoxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (compound 13)

According to Example 12, 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 12.86 g (40.18 mmol) of 3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra instead of galactopyranosyloxy bromide 24.78 g (60.27 mmol) of -O-acetyl- α -D-glucopyranosyloxy bromide gave 13.58 g of the title compound (13) (yield 52%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.1 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t , 1H, J = 9.8Hz), 4.45 (t, 2H, J = 6.0Hz), 4.10 ~ 4.40 (m, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H) , 2.02 (s, 3H), 1.99 (s, 3H), 1.70 ~ 1.80 (m, 2H), 1.25 ~ 1.50 (m, 6H), 0.88 (t, 3H, J = 7.2Hz)

IR (KBr, cm ^-1 ): 2950, 1750, 1620, 1370, 1240

Elemental Analysis for C ₃₁ H ₃₈ O ₁₅

Calculated (%): C 58.13; H 4.41; O 37.47

Found (%): C 58.20; H 4.45; O 37.35

Example 14

3-acetoxy-4-hexyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one (compound 14)

According to Example 12, 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 6.00 g (18.73 mmol) of 3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra instead of galactopyranosyloxy bromide 3.66 g of the title compound (14) are obtained using 11.55 g (28.10 mmol) of -O-acetyl- β -D-mannopyranosyloxy bromide (yield 30%).

¹ H-NHR (DMSO-d ₆ , δ -TMS): 7.78 (d, 1H, J = 8.8 Hz), 7.15 to 7.30 (m, 2H), 5.94 (s, 1H), 5.35 to 5.45 (m, 2H ), 5.13 (t, 1H, J = 10.0 Hz), 4.45 (t, 2H, J = 5.9 Hz), 3.90-4.20 (m, 3H), 2.34 (s, 3H), 2.18 (s, 3H), 2.05 (s, 3H), 2.00 (s, 3H), 1.92 (s, 3H), 1.70 to 1.80 (m, 2H), 1.25 to 1.50 (m, 6H), 0.88 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2950, 1750, 1630, 1370, 1240

Elemental Analysis for C ₃₁ H ₃₈ O ₁₅

Calculated (%): C 58.13; H 4.41; O 37.47

Found (%): C 58.19; H 4.39; O 37.42

Example 15

3-acetoxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 15)

According to Example 12, 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 4.50 g (14.05 mmol) of 3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra instead of galactopyranosyloxy bromide 4.66 g (21.07 mmol) of the title compound (15) are obtained using a yield of 8.66 g (21.07 mmol) of -O-acetyl- α -D-galactopyranosyloxy bromide (yield 51%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 9.2 Hz), 7.05 to 7.15 (m, 2H), 5.66 (d, 1H, J = 7.2 Hz), 5.20- 5.40 (m, 2H), 4.50 to 4.55 (m, 3H), 4.45 (t, 2H, J = 6.2 Hz), 4.12 (t, 2H, J = 6.4 Hz), 2.34 (s, 3H), 2.16 (s , 3H), 2.05 (s, 3H), 2.03 (s, 3H), 1.97 (s, 3H), 1.70-1.80 (m, 2H), 1.25-1.50 (m, 6H), 0.88 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 2930, 1750, 1620, 1370, 1230

Elemental Analysis for C ₃₁ H ₃₈ O ₁₅

Calculated (%): C 58.13; H 4.41; O 37.47

Found (%): C 58.16; H 4.45; O 37.39

Example 16

3-acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (compound 16)

According to Example 12, 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 14.00 g (40.28 mmol) of 3-acetoxy-4-octyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra- instead of galactopyranosyloxy bromide 24.84 g (64.41 mmol) of O-acetyl- α -D-glucopyranosyloxy bromide was used to yield 13.65 g (50% yield) of the title compound (16).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.76 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.05 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.10 ~ 5.15 (m, 1H), 5.04 (t, 1H, J = 9.8Hz) , 4.45 (t, 2H, J = 6.0 Hz), 4.05 to 4.35 (m, 3H), 2.34 (s, 3H), 2.00 to 2.05 (m, 9H), 1.99 (s, 3H), 1.70 to 1.80 (m , 2H), 1.20 ~ 1.50 (m, 10H), 0.85 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 2920, 1740, 1630, 1610, 1370, 1230

Elemental Analysis for C ₃₃ H ₄₂ O ₁₅

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.16; H 6.19; O 35.65

Example 17

3-acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 17)

According to Example 12, 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl- α -D- 14.00 g (40.28 mmol) of 3-acetoxy-4-octyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra- instead of galactopyranosyloxy bromide 24.84 g (60.41 mmol) of O-acetyl- α -D-galactopyranosyloxy bromide was used to yield 14.47 g (53% yield) of the title compound (17).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.76 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.04 (dd, 1H, J = 2.2 Hz, J = 9.0Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 7.2H 5.20 ~ 5.40 (m, 2H), 4.42 (t, 1H, J = 6.4Hz), 4.45 (t, 2H, J = 6.4Hz), 4.11 (d, 2H, J = 6.0Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.03 (s, 3H) , 1.97 (s, 3H), 1.70 to 1.80 (m, 2H), 1.20 to 1.50 (m, 1 OH), 0.85 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 2930, 1750, 1620, 1370, 1230

Elemental Analysis for C ₃₃ H ₄₂ O ₁₅

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.51; H 6.29; O 35.20

Example 18

3-hydroxy-4-butoxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 18)

19.07 g of 3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one in 380 ml of methanol under argon atmosphere 30.63 mmol) was added 3.31 g (61.26 mmol) of sodium methoxide at 5 ° C. and then stirred at room temperature for 1 hour. Then 27.85 g of Amberlyst-15 is added and the mixture is stirred at room temperature for 1 hour. Amberlyst-15 is filtered off and the filtrate is evaporated to yield crystalline product. 10.18 g of the title compound (18) is obtained after reprecipitation with ethanol (yield 81%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.18 (s, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.00-7.10 (m, 2H), 5.20 (d, 1H, J = 5.6 Hz), 4.91 (d, 1H, J = 8.0 Hz), 4.88 (d, 1H, J = 5.2 Hz), 4.67 (t, 1H, J = 5.2 Hz), 4.52 (d, 1H, J = 4.4 Hz), 4.48 (t, 2H, J = 6.4 Hz), 3.40 to 3.75 (m, 6H), 1.65-1.75 (m, 2H), 1.40 to 1.50 (m, 2H), 0.93 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3400, 2950, 2930, 2860, 1680, 1640, 1610, 1250

Elemental Analysis for C ₁₉ H ₂₄ O ₁₀

Calculated (%): C 55.34; H 5.87; O 38.80

Found (%): C 55.41; H 5.81; O 38.78

Example 19

3-hydroxy-4-hexyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (compound 19)

According to Example 18, 3- instead of 3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one 10.94 g (16.81 mmol) of acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one gave the title compound (19 6.66 g) is obtained (yield 90%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.00-7.10 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.47 (t, 2H, J = 6.2 Hz), 3.10-3.75 (m , 6H), 1.65 ~ 1.80 (m, 2H), 1.20 ~ 1.50 (m, 6H), 0.87 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1700, 1640, 1610, 1260

Elemental Analysis for C ₂₁ H ₂₈ O ₁₀

Calculated (%): C 57.27; H 6.41; O 36.33

Found (%): C 55.25; H 6.49; O 38.46

Example 20

3-hydroxy-4-hexyloxy-7- ( α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one (Compound 20)

According to Example 18, 3- instead of 3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one 13.40 g (20.60 mmol) of acetoxy-4-hexyloxy-7- (tetra-O-acetyl- α -D-mannopyranosyloxy) -2H-1-benzopyran-2-one gave the title compound ( 7.62 g of 20) is obtained (yield 84%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.47 (t, 2H, J = 6.4 Hz), 3.85 (s, 1H), 3.20-3.75 (m, 6H), 1.65-1.80 (m, 2H), 1.20-1.50 (m, 6H), 0.87 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₁ H ₂₈ O ₁₀

Calculated (%): C 57.27; H 6.41; O 36.33

Found (%): C 57.38; H 6.40; O 36.22

Example 21

3-hydroxy-4-hexyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 21)

3-acetoxy instead of 3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one according to example 18 12.57 g (19.32 mmol) of methoxy-4-hexyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one was used to provide the title compound ( 7.55 g (yield 89%) is obtained.

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.00-7.10 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.47 (t, 2H, J = 6.6 Hz), 3.25-3.65 (m , 6H), 1.70 ~ 1.80 (m, 2H), 1.20 ~ 1.50 (m, 6H), 0.87 (t, 3H, J = 7.2Hz)

IR (KBr, cm ^-1 ): 3400, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₁ H ₂₈ O ₁₀

Calculated (%): C 57.27; H 6.41; O 36.33

Found (%): C 57.16; H 6.46; O 36.38

Example 22

3-hydroxy-4-octyloxy-7- ( β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one (compound 22)

According to Example 18, 3- instead of 3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one 10.95 g (16.13 mmol) of acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-glucopyranosyloxy) -2H-1-benzopyran-2-one gave the title compound (22 6.95 g) is obtained (yield 92%).

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.19 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.00-7.10 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J = 7.2 Hz), 4.59 (bs, 1H), 4.46 (t, 2H, J = 6.4 Hz), 3.10-3.75 (m , 6H), 1.65 ~ 1.80 (m, 2H), 1.15 ~ 1.50 (m, 10H), 0.85 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 3350, 2920, 2850, 1700, 1640, 1610, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 58.97; H 6.88: 0 34.15

Found (%): C 58.92; H 6.87; O 34.21

Example 23

3-hydroxy-4-octyloxy-7- ( β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one (compound 23)

According to Example 18, 3- instead of 3-acetoxy-4-butoxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one 20.67 g (30.46 mmol) of acetoxy-4-octyloxy-7- (tetra-O-acetyl- β -D-galactopyranosyloxy) -2H-1-benzopyran-2-one gave the title compound ( 12.47 g of 23) are obtained (yield 87%).

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.15 (bs, 1H), 7.60 (d, 1H, J = 8.4 Hz), 7.00-7.10 (m, 2H), 5.21 (bs, 1H), 4.91 (d, 1H, J = 8.0 Hz), 4.88 (bs, 1H), 4.66 (bs, 1H), 4.52 (d, 1H, J = 3.6 Hz), 4.47 (t, 2H, J = 6.6 Hz), 3.10-3.75 (m, 6H), 1.65-1.80 (m, 2H), 1.15-1.50 (m, 10H), 0.85 (t, 3H, J = 6.6 Hz)

IR (KBr, cm ^-1 ): 3400, 2910, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 58.97; H 6.88; O 34.15

Found (%): C 58.99; H 6.92: 0 34.09

(Examples 24 to 160)

The following table shows the 7-glycopyranosyloxy benzopyran derivatives (24) to (160) obtained by the method described in the Examples.

The abbreviations used in the table are:

Glc glucopyranosyl group

Man Mannpyranosyl Group

Gal galactopyranosyl group

Protection group of R ₄ sugar

Table 1

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Compound 24

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1 H). 5.42 (s, 2H), 5.35-5.25 (m, 2H), 5.20 (m, 8H), 5.12 (t, 1H, J = 8.0 Hz), 4.95 (d, 1H, J = 8.0 Hz), 4.30-4.20 (m, 2H), 3.85-3.81 (m, 1H), 3.73 (s, 3H)

IR (KBr, cm ^-1 ): 1645, 1600, 1440, 1380

Elemental Analysis for C ₅₁ H ₄₈ O ₁₀

Calculated (%): C 74.62; H 5.89; O 19.49

Found (%): C 74.53; H 5.88; O 19.59

Compound 25

¹ H-NMR (OMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.15 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.82 ( s, 1H), 5.42 (s, 2H), 5.35-5.25 (m, 2H), 5.22 (m, 8H), 5.17 (t, 1H, J = 8.0 Hz), 4.93 (d, 1H, J = 8.0 Hz ), 4.40 (t, 2H, J = 6.8 Hz), 4.30-4.21 (m, 2H), 3.85-3.81 (m, 1H), 1.75-1.24 (m, 4H), 0.93 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1645, 1610, 1435, 1380

Elemental Analysis for C ₅₄ H ₅₄ O ₁₀

Calculated (%): C 75.15; H 6.31; O 18.54

Found (%): C 75.23; H 6.28; O 18.49

Compound 26

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.71 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 5.42 (s, 2H), 5.35-5.25 (m, 2H), 5.10 (t, 1H, J = 8.0 Hz), 4.95 (d, 1H, J = 8.0 Hz), 4.52 (t, 2H , J = 6.5Hz), 4.30 ~ 4.20 (m, 2H), 3.85 ~ 3.80 (m, 1H), 2.20 ~ 2.00 (m, 12H), 1.78 ~ 1.28 (m, 8H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1765, 1645, 1610, 1440, 1380

Elemental Analysis for C ₃₆ H ₄₂ O ₁₄

Calculated (%): C 61.89; H 6.06; O 32.05

Found (%): C 61.73; H 6.18; O 32.09

Compound 27

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.62-7.20 (m, 5H), 6.90 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 5.42 (s, 2H), 5.35-5.25 (m, 2H), 5.10 (t, 1H, J = 8.0 Hz), 4.98 (d, 1H, J = 8.0 Hz), 4.50 (t, 2H , J = 6.5Hz), 4.28 ~ 4.20 (m, 2H), 3.84 Å '3.80 (m, 1H), 2.20 ~ 1.98 (m, 12H), 180 ~ 1.25 (m, 12H), 0.89 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 1765, 1645, 1600, 1445, 1380

Elemental Analysis for C ₃₈ H ₄₆ O ₁₄

Calculated (%): C 62.80; H 6.38; O 30.82

Found (%): AFC 62.83; H 6.43; O 30.74

Compound 28

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.79 ( s, 1H), 5.42 (s, 2H), 5.35-5.25 (m, 2H), 5.08 (t, 1H, J = 8.0 Hz), 4.97 (d, 1H, J = 8.0 Hz), 4.52 (t, 2H , J = 6.5Hz), 4.30 ~ 4.18 (m, 2H), 3.85 ~ 3.80 (m, 1H), 2.22 ~ 2.00 (m, 12H), 1.80 ~ 1.20 (m, 16H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1760, 1645, 1610, 1430, 1380

Elemental Analysis for C ₄₀ H ₅₀ O ₁₄

Calculated (%): C 63.65; H 6.68; O 29.67

Found (%): C 63.53; H 6.78; O 29.69

Compound 29

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.73 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 5.42 (s, 2H), 5.35-5.25 (m, 2H), 5.12 (t, 1H, J = 8.0 Hz), 4.95 (d, 1H, J = 8.0 Hz), 4.52 (t, 2H , J = 6.5Hz), 4.27 ~ 4.18 (m, 2H), 3.85 ~ 3.80 (m, 1H), 2.20 ~ 2.00 (m, 12H), 1.83 ~ 1.25 (m, 20H), 0.90 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1765, 1640, 1605, 1440, 1380

Elemental Analysis for C ₄₂ H ₅₄ O ₁₄

Calculated (%): C 64.44; H 6.95; O 28.61

Found (%): C 64.53; H 6.78; O 28.69

Compound 30

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.74 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 5.43 (s, 2H), 5.35 ~ 5.23 (m, 2H), 5.12 (t, 1H, J = 8.0Hz), 4.97 (d, 1H, J = 8.0Hz), 4.51 (m, 1H ), 4.26 to 4.16 (m, 2H), 3.83 to 3.78 (m, 1H), 2.22 to 2.00 (m, 12H), 1.03 (d, 6H, J = 7.4 Hz)

IR (KBr, cm ^-1 ): 1770, 1650, 1605, 1435, 1380

Elemental Analysis for C ₃₃ H ₃₆ O ₁₄

Calculated (%): C 60.36; H 5.53; O 34.11

Found (%): C 60.33; H 5.68; O 33.99

Compound 31

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.60 to 7.18 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 5.44 (s, 2H), 5.32-5.24 (m, 2H), 5.12 (t, 1H, J = 8.0 Hz), 5.00 (m, 1H), 4.95 (d, 1H, J = 8.0 Hz ), 4.28-4.18 (m, 2H), 3.84-3.80 (m, 1H), 2.23-1.26 (m, 21H), 0.96 (d, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 1760, 1640, 1605, 1445, 1380

Elemental Analysis for C ₃₇ H ₄₂ O ₁₄

Calculated (%): C 62.53; H 5.96; O 31.51

Found (%): C 62.83; H 5.75; O 31.42

Compound 32

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.72 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.87 (d, 1H, J = 8.8 Hz), 6.75 ( s, 1H), 6.44 (dd, 1H, J = 17.5 Hz, J = 9.4 Hz), 5.42 (s, 2H), 5.34-5.24 (m, 2H), 5.12 (t, 1H, J = 8.0 Hz), 4.95 (d, 1H, J = 8.0 Hz), 4.28 to 4.16 (m, 2H), 4.13 (dd, 1H, J = 17.6 Hz, J = 2.0 Hz), 3.91 (dd, 1H, J = 9.4 Hz, J = 1.9 Hz), 3.85 to 3.79 (m, 1H), 2.19 to 2.00 (m, 12H)

IR (KBr, cm ^-1 ): 1765, 1635, 1600, 1440, 1375

Elemental Analysis for C ₃₂ H ₃₂ O ₁₄

Calculated (%): C 60.00; H 5.04; O 34.96

Found (%): C 59.93; H 5.08; O 34.99

Compound 33

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.71 (d, 1H, J = 8.8 Hz), 7.58-7.20 (m, 5H), 6.86 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 5.42 (s, 2H), 5.35-5.25 (m, 4H), 5.10 (t, 1H, J = 8.0 Hz), 4.97 (d, 1H, J = 8.0 Hz), 4.28-4.22 (m , 4H), 3.86 ~ 3.81 (m, 1H), 2.30 ~ 1.94 (m, 16H), 0.98 (t, 3H, J = 7.2Hz)

IR (KBr, cm ^-1 ): 1765, 1650, 1610, 1440, 1370

Elemental Analysis for C ₃₆ H ₄₀ O ₁₄

Calculated (%): C 62.06; H 5.79; O 32.15

Found (%): C 62.13; H 5.78; O 32.09

Compound 34

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.74 (d, 1H, J = 8.8 Hz), 7.62-7.22 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.76 ( s, 1H), 5.42 (s, 2H), 5.36-5.26 (m, 3H), 5.10 (m, 2H), 4.95 (d, 1H, J = 8.0 Hz), 4.27-4.17 (m, 2H), 4.12 (d, 2H, J = 8.6 Hz), 3.86-3.80 (m, 1H), 2.19-1.98 (m, 16H), 1.68 (s, 6H), 1.59 (s, 3H)

IR (KBr, cm ^-1 ): 1760, 1645, 1605, 1440, 1370

Elemental Analysis for C ₄₀ H ₄₆ O ₁₄

Calculated (%): C 63.99; H 6.18; O 29.83

Found (%): C 63.83; H 6.24; O 29.93

Compound 35

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.67 (d, 1H, J = 8.8 Hz), 7.55 to 7.15 (m, 25H), 6.73 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 5.58 (s, 2H), 5.37 ~ 5.24 (m, 2H), 5.15 (m, 8H), 5.10 (t, 1H, J = 8.0Hz), 4.96 (d, 1H, J = 8.0Hz ), 4.51 (t, 2H, J = 6.8 Hz), 4.24 to 4.19 (m, 2H), 3.86 to 3.82 (m, 1H), 1.77 to 1.20 (m, 12H), 0.91 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1645, 1610, 1440, 1380

Elemental Analysis for C ₅₈ H ₆₂ O ₁₀

Calculated (%): C 75.79; H 6.80; O 17.41

Found (%): C 75.83; H 6.78: 0 17.39

Compound 36

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.70 ~ 7.15 (m, 30H), 6.90 (d, 1H, J = 8.8 Hz), 6.79 ( s, 1H), 5.45 (s, 2H), 5.35-5.25 (m, 2H), 5.17 (m, 10H), 5.08 (t, 1H, J = 8.0 Hz), 4.90 (d, 1H, J = 8.0 Hz ), 4.29-4.21 (m, 2H), 3.87-3.78 (m, 1H)

IR (KBr, cm ^-1 ): 1640, 1605, 1445, 1370

Elemental Analysis for C ₅₇ H ₅₂ O ₁₀

Calculated (%): C 76.32; H 5.84; O 17.84

Found (%): C 76.53; H 5.78; O 17.69

Compound 37

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.32 (bs, 1H), 7.59 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.39 (bs, 1H), 5.11 (bs, 1H), 5.06 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.60 (bs, 1H), 4.25 (t, 2H, J = 6.2 Hz), 3.76-3.10 (m , 6H), 180 ~ 1.20 (m, 4H), 0.88 (t, 3H), J = 7.0Hz)

IR (KBr, cm ^-1 ): 3350, 2960, 2920, 2840, 1700, 1645, 1610, 1260

Elemental Analysis for C ₁₉ H ₂₄ O ₁₀

Calculated (%): C 55.33; H 5.87, O 38.80

Found (%): C 55.29; H 5.89; O 38.82

Compound 38

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.45 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.11-7.02 (m, 2H), 5.35 (bs, 1H), 5.08 (bs, 1H), 5.04 (bs, 1H), 4.95 (d, 1H, J = 7.2 Hz), 4.57 (bs, 1H), 4.42 (t, 2H, J = 6.4 Hz), 3.82-3.12 (m , 6H), 1.80 ~ 1.20 (m, 8H), 0.85 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 3345, 2920, 2850, 1710, 1635, 1610, 1250

Elemental Analysis for C ₂₁ H ₂₈ O ₁₀

Calculated (%): C 57.26; H 6.41; O 36.33

Found (%): C 57.20; H 6.35; O 36.45

Compound 39

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.40 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.12-7.02 (m, 2H), 5.37 (bs, 1H), 5.10 (bs, 1H), 5.04 (bs, 1H), 4.95 (d, 1H, J = 7.2 Hz), 4.56 (bs, 1H), 4.41 (t, 2H, J = 6.4 Hz), 3.80-3.12 (m , 6H), 1.82 ~ 1.13 (m, 12H), 0.85 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 3350, 2920, 2845, 1700, 1635, 1610, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 58.96; H 6.89; O 34.15

Found (%): C 59.06; H 6.77; O 34.17

Compound 40

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.20 (bs, 1H), 7.62 (d, 1H, J = 8.8 Hz), 7.12-7.02 (m, 2H), 5.33 (bs, 1H), 5.12 (bs, 1H), 5.04 (bs, 1H), 4.95 (d, 1H, J = 7.2 Hz), 4.56 (bs, 1H), 4.38 (t, 2H, J = 6.4 Hz), 3.75-3.10 (m , 6H), 1.85-1.15 (m, 16H), 0.85 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 3340, 2925, 2845, 1705, 1650, 1620, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 60.47; H 7.31, O 32.22

Found (%): C 60.45; H 7.35; O 32.20

Compound 41

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.45 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.39 (bs, 1H), 5.13 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J = 7.2 Hz), 4.57 (bs, 1H), 4.25 (t, 2H, J = 6.4 Hz), 3.80-3.18 (m , 6H), 180 ~ 1.60 (m, 2H), 1.52 ~ 1.12 (m, 18H), 0.88 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 3350, 2910, 2850, 1700, 1650, 1610, 1250

Elemental Analysis for C ₂₇ H ₄₀ O ₁₀

Calculated (%): C 61.81, H 7.69; O 30.50

Found (%): C 61.77; H 7.55; O 30.68

Compound 42

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.43 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.35 (bs, 1H), 5.10 (bs, 1H), 5.05 (bs, 1H), 4.99 (d, 1H, J = 6.8 Hz), 4.62 (bs, 1H), 4.45 (m, 1H), 3.75-3.10 (m, 6H), 1.05 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 3330, 3300, 2940, 2850, 1700, 1600, 1250

Elemental Analysis for C ₁₈ H ₂₂ O ₁₀

Calculated (%): C 54.27; H 5.57; O 40.16

Found (%): C 54.28; H 5.69; O 40.03

Compound 43

¹ H-NMR (CDCl ₃ , δ -TMS): 10.38 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.01 (m, 2H), 5.35 (bs, 1H), 5.10 ( bs, 1H), 5.03 (bs, 1H), 4.98 (m, 1H), 4.93 (d, 1H, J = 6.8 Hz), 4.53 (bs, 1H), 3.80-3.09 (m, 6H), 2.00-1.22 (m, 9H), 0.95 (d, 3H, J = 6.5 Hz)

IR (KBr, cm ^-1 ): 3335, 3300, 2955, 2850, 1710, 1620, 1250

Elemental Analysis for C ₂₂ H ₂₈ O ₁₀

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.35; H 6.29; O 35.36

Compound 44

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.48 (bs, 1H), 7.65 (d, 1H, J = 8.8 Hz), 7.13-7.03 (m, 2H), 6.57 (dd, 1H, J = 17.5 Hz, J = 9.5 Hz), 5.35 (bs, 1H), 5.15 (bs, 1H), 5.08 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.17 (dd, 1H, J = 17.5Hz, J = 2.0Hz), 3.95 (dd, 1H, J = 9.5Hz, J = 2.0Hz), 3.80 ~ 3.12 (m, 6H)

IR (KBr, cm ^-1 ): 3340, 3310, 2950, 2845, 1700, 1610, 1250

Elemental Analysis for C ₁₇ H ₁₈ O ₁₀

Calculated (%): C 53.40; H 4.75; O 41.85

Found (%): C 53.57; H 4.69; O 41.74

Compound 45

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.40 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.50 (m, 1H), 5.34 (m, 2H), 5.11 (bs, 1H), 5.03 (bs, 1H), 4.98 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.27 (t, 2H, J = 6.2 Hz ), 3.83 to 3.15 (m, 6H), 2.25 to 1.96 (m, 4H), 0.99 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 1710, 1640, 1615, 1260

Elemental Analysis for C ₂₁ H ₂₆ O ₁₀

Calculated (%): C 57.53; H 5.98; O 36.49

Found (%): C 57.65; H 5.89; O 36.46

Compound 46

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.35 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12-7.00 (m, 2H), 5.38 (m, 1H), 5.34 (bs, 1H), 5.10 (m, 2H), 5.05 (bs, 1H), 4.98 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.10 (d, 2H, J = 8.5 Hz ), 3.80-3.15 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm ^-1 ): 3345, 2950, 2920, 1705, 1640, 1610, 1260

Elemental Analysis for C ₂₅ H ₃₂ O ₁₀

Calculated (%): C 60.96; H 6.55; O 32.49

Found (%): C 60.85; H 6.70; O 32.45

Compound 47

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.50 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.30-7.15 (m, 5H), 7.10-7.00 (m, 2H ), 5.35 (bs, 1H), 5.25 (s, 2H), 5.11 (bs, 1H), 5.00 (bs, 1H), 4.93 (d, 1H, J = 6.8 Hz), 4.55 (bs, 1H), 3.80 ~ 3.10 (m, 6H)

IR (KBr, cm ^-1 ): 3340, 3300, 2955, 2850, 1710, 1620, 1260

Elemental Analysis for C ²² H ²² O ¹⁰

Calculated (%): C 59.19; H 4.97; O 35.84

Found (%): C 59.15; H 4.89; O 35.96

Compound 48

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.71 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.75 ( s, 1H), 6.00 (S, 1H), 5.54 (m, 2H), 5.43 (s, 2H), 5.39 (m, 1H), 5.20 (m, 8H), 4.24 (m, 2H), 4.15 (s , 1H), 3.73 (s, 3H)

IR (KBr, cm ^-1 ): 1645, 1610, 1440, 1380

Elemental Analysis for C ₅₁ H ₄₈ O ₁₀

Calculated (%): C 74.62; H 5.89; O 19.49

Found (%): C 74.56; H 5.84; O 19.60

Compound 49

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.15 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.75 ( s, 1H), 6.00 (S, 1H), 5.55 (s, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 5.22 (m, 8H), 4.42 (t, 2H, J = 6.7 Hz ), 4.25 (m, 2H), 4.15 (s, 1H), 1.75-1.24 (m, 4H), 0.93 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1645, 1610, 1435, 1380

Elemental Analysis for C ₅₄ H ₅₄ O ₁₀

Calculated (%): C 75.15; H 6.31; O 18.54

Found (%): C 75.23; H 6.28; O 18.49

Compound 50

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.79 ( s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 4.50 (t, 2H, J = 6.5 Hz), 4.24 (m, 2H ), 4.15 (s, 1H), 2.18-1.98 (m, 12H), 1.80-1.30 (m, 8H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1765, 1645, 1610, 1435, 1380

Elemental Analysis for C ₃₆ H ₄₂ O ₁₄

Calculated (%): C 61.89; H 6.06; O 32.05

Found (%): C 61.74; H 6.10; O 32.06

Compound 51

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.62-7.20 (m, 5H), 6.90 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.44 (s, 2H), 5.41 (m, 1H), 4.50 (t, 2H, J = 6.5 Hz), 4.25 (m, 2H ), 4.13 (s, 1H), 2,20-1.98 (m, 12H), 1.80-1.25 (m, 12H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1760, 1640, 1600, 1445, 1380

Elemental Analysis for C ₃₈ H ₄₆ O ₁₄

Calculated (%): C 62.80; H 6.38; O 30.82

Found (%): C 62.87; H 6.33; O 30.80

Compound 52

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.03 (s, 1H), 5.57 (m, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 4.52 (t, 2H, J = 6.5 Hz), 4.25 (m, 2H ), 4.13 (s, 1H), 2.23-2.00 (m, 12H), 1.81-1.21 (m, 16H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1760, 1635, 1600, 1430, 1380

Elemental Analysis for C ₄₀ H ₅₀ O ₁₄

Calculated (%): C 63.65; H 6.68; O 29.67

Found (%): C 63.53; H 6.85; O 29.52

Compound 53

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.43 (s, 2H), 5.38 (m, 1H), 4.51 (t, 2H, J = 6.5 Hz), 4.23 (m, 2H ), 4.12 (s, 1H), 2.20-2.02 (m, 12H), 1.84-1.24 (m, 20H), 0.90 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1760, 1640, 1610, 1440, 1380

Elemental Analysis for C ₄₂ H ₅₄ O ₁₄

Calculated (%): C 64.44; H 6.95; O 28.61

Found (%): C 64.47; H 6.88; O 28.65

Compound 54

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.71 (d, 1H, J = 8.8 Hz), 7.56-7.7.1 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.00 (s, 1H), 5.59 (m, 2H), 5.42 (s, 2H), 5.39 (m, 1H), 4.50 (m, 1H), 4.23 (m, 2H), 4.12 (s , 1H), 2.22-2.00 (m, 12H), 1.05 (d, 6H, J = 7.4Hz)

IR (KBr, cm ^-1 ): 1770, 1645, 1605, 1430, 1380

Elemental Analysis for C ₃₃ H ₃₆ O ₁₄

Calculated (%): C 60.36; H 5.53; O 34.11

Found (%): C 60.39; H 5.64; O 33.97

Compound 55

¹ H-NMR (OMSO-d ₆ , δ -TMS): 7.72 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.44 (s, 2H), 5.41 (m, 1H), 5.00 (m, 1H), 4.22 (m, 2H), 4.13 (s , 1H), 2.23-1.26 (m, 21H), 0.96 (d, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 1750, 1640, 1600, 1445, 1380

Elemental Analysis for C ₃₇ H ₄₂ O ₁₄

Calculated (%): C 62.53; H 5.96; O 31.51

Found (%): C 62.63; H 5.85, O 31.52

Compound 56

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.73 (d, 1H, J = 8.8 Hz), 7.59-7.18 (m, 5H), 6.87 (d, 1H, J = 8.8 Hz), 6.74 ( s, 1H), 6.44 (dd, 1H, J = 17.5 Hz, J = 9.4 Hz), 6.00 (s, 1H), 5.50 (m, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 4.24 (m, 2H), 4.15 (s, 1H), 4.13 (dd, 1H, J = 17.6 Hz, J = 2.0 Hz), 3.91 (dd, 1H, J = 9.4 Hz, J = 1.9 Hz), 2.22- 2.00 (m, 12H)

IR (KBr, cm ^-1 ): 1765, 1640, 1600, 1435, 1375

Elemental Analysis for C ₃₂ H ₃₂ O ₁₄

Calculated (%): C 60.00; H 5.04; O 34.96

Found (%): C 59.97; H 5.10; O 34.93

Compound 57

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.58-7.20 (m, 5H), 6.86 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 6.00 (s, 1H), 5.50 (m, 2H), 5.43 (s, 2H), 5.41 (m, 1H), 5.34 (m, 2H), 4.26 (t, 2H, J = 6.2 Hz ), 4.23 (m, 2H), 4.14 (s, 1H), 2.30-1.96 (m, 16H), 0.98 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 1760, 1650, 1610, 1440, 1370

Elemental Analysis for C ₃₆ H ₄₀ O ₁₄

Calculated (%): C 62.06; H 5.79; O 32.15

Found (%): C 62.03, H 5.88; O 32.09

Compound 58

¹ H-NMR (OMSO-d ₆ , δ -TMS): 7.72 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.76 ( s, 1H), 6.02 (s, 1H), 5.50 (m, 2H), 5.44 (s, 2H), 5.41 (m, 1H), 5.35 (m, 1H), 5.13 (m, 1H), 4.23 (m , 2H), 4.14 (s, 1H), 4.12 (d, 2H, J = 8.6 Hz), 2.20-1.98 (m, 16H), 1.68 (s, 6H), 1.58 (s, 3H)

IR (KBr, cm ^-1 ): 1765, 1645, 1600, 1440, 1370

Elemental Analysis for C ₄₀ H ₄₆ O ₁₄

Calculated (%): C 63.99; H 6.18; O 29.83

Found (%): C 63.88; H 6.23; O 29.89

Compound 59

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.69 (d, 1H, J = 8.8 Hz), 7.55 to 7.15 (m, 25H), 6.73 (d, 1H, J = 8.8 Hz), 6.81 ( s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.40 (m, 1H), 5.36 (s, 2H), 5.15 (m, 8H), 4.49 (t, 2H, J = 6.8 Hz ), 4.23 (m, 2H), 4.14 (s, 1H), 180-1.20 (m, 12H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1650, 1610, 1435, 1380

Elemental Analysis for C ₅₈ H ₆₂ O ₁₀

Calculated (%): C 75.79, H 6.80; O 17.41

Found (%): C 75.87; H 6.74; O 17.39

Compound 60

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.15 (m, 30H), 6.90 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.46 (s, 2H), 5.41 (m, 1H), 5.17 (m, 10H), 4.22 (m, 2H), 4.15 (s , 1H)

IR (KBr, cm ^-1 ): 1640, 1600, 1445, 1370

Elemental Analysis for C ₅₇ H ₅₂ O ₁₀

Calculated (%): C 76.32; H 5.84; O 17.84

Found (%): C 76.56; H 5.79; O 17.65

Compound 61

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.13 (s, 1H), 9.20 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.15 (d, 1H, J = 2.4 Hz), 7.10 (dd, 1H, J = 2.2 Hz, J = 9.0 Hz), 5.47 (s, 1H), 5.09 (bs, 1H), 4.85 (bs, 1H), 4.80 (bs, 1H), 3.85 ( s, 1H), 3.75-3.25 (m, 6H)

IR (KBr, cm ^-1 ): 3340, 2950, 2910, 2850, 1690, 1620, 1610, 1250

Elemental Analysis for C ₁₅ H ₁₆ O ₁₀

Calculated (%): C 50.56; H 4.53; O 44.91

Found (%): C 50.42, H 4.58; O 45.00

Compound 62

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.35 (bs, 1H), 7.57 (d, 1H, J = 8.8 Hz), 7.14 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.08 (bs, 1H), 4.90 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J = 6.4 Hz), 3.87 (s, 1H), 3.78-3.20 (m, 6H), 1.75-1.20 (m, 4H), 0.86 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3345, 2950, 2900, 2850, 1690, 1635, 1600, 1250

Elemental Analysis for C ₁₉ H ₂₄ O ₁₀

Calculated (%): C 55.33; H 5.87; O 38.80

Found (%): C 55.35; H 5.90; O 38.75

Compound 63

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.15 (bs, 1H), 7.56 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.09 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.05 (bs, 1H), 4.90 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J = 6.4 Hz), 3.86 (s, 1H), 3.75-3.20 (m, 6H), 1.70-1.30 (m, 8H), 0.90 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3355, 2950, 2900, 2850, 1670, 1630, 1610, 1250

Elemental Analysis for C ₂₁ H ₂₈ O ₁₀

Calculated (%): C 57.26; H 6.41; O 36.33

Found (%): C 57.35; H 6.35; O 36.30

Compound 64

₁ H-NMR (DMSO-d ₆ , δ -TMS): 10.25 (bs, 1H), 7.58 (d, 1H, J = 8.8 Hz), 7.14 (d, 1H, J = 2.4 Hz), 7.09 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.08 (bs, 1H), 4.89 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J = 6.4 Hz), 3.87 (s, 1H), 3.76 to 3.23 (m, 6H), 1.80 to 1.30 (m, 12H), 0.87 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2910, 2850, 1680, 1635, 1610, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 58.96, H 6.89; O 34.15

Found (%): C 58 85; H 6.85; O 34.30

Compound 65

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.05 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.15 (d, 1H, J = 2.4 Hz), 7.09 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.45 (s, 1H), 5.09 (bs, 1H), 4.85 (bs, 1H), 4.74 (bs, 1H), 4.42 (t, 2H, J = 6.4 Hz), 3.85 (s, 1H), 3.80-3.25 (m, 6H), 1.75-1.20 (m, 16H), 0.88 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2940, 2920, 2850, 1680, 1630, 1610, 1245

Elemental Analysis for C ₂₅ H ₃₆ O ₁₀

Calculated (%): C 60.47, H 7.31; O 32.22

Found (%): C 60.45: H 7.40; O 32.15

Compound 66

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.85 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.08 (bs, 1H), 4.90 (bs, 1H), 4.80 (bs, 1H), 4.42 (t, 2H, J = 6.4 Hz), 3.88 (s, IH), 3.70 to 3.15 (m, 6H), 1.95 to 1.20 (m, 20H), 0.85 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2915, 2850, 1685, 1630, 1600, 1250

Elemental Analysis for C ₂₇ H ₄₀ O ₁₀

Calculated (%): C 61.81; H 7.69; O 30.50

Found (%): C 61.75, H 7.55, O 30.70

Compound 67

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.98 (bs, 1H), 7.63 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.08 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.87 (bs, 1H), 4.76 (bs, 1H), 4.43 (m, 1H), 3.88 ( s, 1H), 3.78-3.12 (m, 6H), 1.07 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 3330, 2950, 2910, 2845, 1690, 1630, 1615, 1250

Elemental Analysis for C ₁₈ H ₂₂ O ₁₀

Calculated (%): C 54.27; H 5.57; O 40.16

Found (%): C 54.18; H 5.65: 0 40.17

Compound 68

¹ H-NMR (CDCl ₃ , δ- TMS): 10.00 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.89 (bs, 1H), 4.76 (bs, 1H), 3.75 ~ 3.25 (m, 6H), 2.25 ~ 1.20 (m, 9H), 0.97 (d, 3H, J = 6.7 Hz)

IR (KBr, cm ^-1 ): 3335, 2940, 2920, 2855, 1690, 1625, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₈ O ₁₀

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.33; H 6.34; O 35.33

Compound 69

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.10 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.13 (d, 1H, J = 2.4 Hz), 7.08 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 6.45 (dd, 1H, J = 17.5Hz, J = 9.5Hz), 5.50 (s, 1H), 5.10 (bs, 1H), 4.87 (bs, 1H) , 4.77 (bs, 1H), 4.13 (dd, 1H, J = 17.5 Hz, J = 2.0 Hz), 3.95 (dd, 1H, J = 9.5 Hz, J = 2.0 Hz), 3.87 (s, 1H), 3.76 ~ 3.21 (m, 6H)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2840, 1695, 1630, 1610, 1250

Elemental Analysis for C ₁₇ H ₁₈ O ₁₀

Calculated (%): C 53.40; H 4.75; O 41.85

Found (%): C 53.43; H 4.80; O 41.77

Compound 70

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.78 (bs, 1H), 7.58 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.54 (m, 1H), 5.35 (m, 2H), 5.08 (bs, 1H), 4.85 (bs, 1H), 4.78 (bs, 1H), 4.27 ( t, 2H, J = 6.3Hz), 3.88 (s, 1H), 3.70 ~ 3.25 (m, 6H), 2.25 ~ 1.90 (m, 4H), 0.99 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3340, 2950, 2910, 2850, 1685, 1630, 1615, 1250

Elemental Analysis for C ₂₁ H ₂₆ O ₁₀

Calculated (%): C 57.53, H 5.98; O 36.49

Found (%): C 57.60; H 5.83; O 36.57

Compound 71

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.95 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.41 (m, 1H), 5.16 (m, 1H), 5.09 (bs, 1H), 4.87 (bs, 1H), 4.77 ( bs, 1H), 4.10 (d, 2HJ = 8.5 Hz), 3.85 (s, 1H), 3.75-3.25 (m, 6H), 2.00 (m, 4H), 1.64 (s, 6H), 1.58 (s, 3H )

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2845, 1690, 1620, 1600, 1250

Elemental Analysis for C ₂₅ H ₃₂ O ₁₀

Calculated (%): C 60.96; H 6.55; O 32.49

Found (%): C 60.89; H 6.60; O 32.51

Compound 72

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.30 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.38 (m, 5H), 7.15 (d, 1H, J = 2.4 Hz), 7.09 (dd, 1H, J = 2.2 Hz, J = 9.0 Hz), 5.47 (s, 1H), 5.25 (s, 2H), 5.07 (bs, 1H), 4.90 (bs, 1H), 4.79 ( bs, 1H), 3.85 (s, 1H), 3.76-3.20 (m, 6H)

IR (KBr, cm ^-1 ): 3335, 2960, 2930, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₂ O ₁₀

Calculated (%): C 59.19; H 4.97; O 35.84

Found (%): C 59.25; H 4.89; O 35.86

Compound 73

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.71 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.75 ( s, 1H), 6.00 (S, 1H), 5.54 (m, 2H), 5.43 (s, 2H), 5.39 (s, 1H), 5.25-5.15 (m, 9H), 4.20-4.11 (m, 2H) , 3.73 (s, 3 H)

IR (KBr, cm ^-1 ): 1645, 1610, 1440, 1380

Elemental Analysis for C ₅₁ H ₄₈ O ₁₀

Calculated (%): C 74.62; H 5.89; O 19.49

Found (%): C 74.56; H 5.84; O 19.60

Compound 74

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.15 (m, 25H), 6.88 (d, 1H, J = 8.8 Hz), 6.75 ( s, 1H), 6.00 (S, 1H), 5.55 (s, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.26-5.16 (m, 9H), 4.42 (t, 2H, J = 6.7 Hz), 4.22 to 4.09 (m, 2H), 1.75 to 1.24 (m, 4H), 0.93 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1645, 1610, 1435, 1380

Elemental Analysis for C ₅₄ H ₅₄ O ₁₀

Calculated (%): C 75.15; H 6.31; O 18.54

Found (%): C 75.23; H 6.28; O 18.49

Compound 75

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.79 ( s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.24-5.16 (m, 1H), 4.50 (t, 2H, J = 6.5 Hz), 4.20 to 4.08 (m, 2H), 2.18 to 1.98 (m, 12H), 180 to 1.30 (m, 8H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1765, 1645, 1610, 1435, 1380

Elemental Analysis for C ₃₆ H ₄₂ O ₁₄

Calculated (%): C 61.89; H 6.06; O 32.05

Found (%): C 61.74; H 6.10; O 32.06

Compound 76

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.62-7.20 (m, 5H), 6.90 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.44 (s, 2H), 5.41 (s, 1H), 5.22-5.14 (m, 1H), 4.50 (t, 2H, J = 6.5 Hz), 4.20 to 4.10 (m, 2H), 2.20 to 1.98 (m, 12H), 180 to 1.25 (m, 12H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1760, 1640, 1600, 1445, 1380

Elemental Analysis for C ₃₈ H ₄₆ O ₁₄

Calculated (%): C 62.80; H 6.38; O 30.82

Found (%): C 62.87; H 6.33; O 30.80

Compound 77

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.88 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.03 (s, 1H), 5.57 (m, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.23-5.15 (m, 1H), 4.52 (t, 2H, J = 6.5Hz), 4.21 ~ 4.08 (m, 2H), 2.23 ~ 2.00 (m, 12H), 1.81 ~ 1.21 (m, 16H), 0.89 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 1760, 1635, 1600, 1430, 1380

Elemental Analysis for C ₄₀ H ₅₀ O ₁₄

Calculated (%): C 63.65; H 6.68; O 29.67

Found (%): C 63.63; H 6.85; O 29.52

Compound 78

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.43 (s, 2H), 5.38 (s, 1H), 5.22-5.13 (m, 1H), 4.51 (t, 2H, J = 6.5 Hz), 4.20 to 4.09 (m, 2H), 2.20 to 2.02 (m, 12H), 1.84 to 1.24 (m, 20H), 0.90 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1760, 1640, 1610, 1440, 1380

Elemental Analysis for C ₄₂ H ₅₄ O ₁₄

Calculated (%): C 64.44; H 6.95; O 28.61

Found (%): C 64.47; H 6.88; O 28.65

Compound 79

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.71 (d, 1H, J = 8.8 Hz), 7.56-7.7.1 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.00 (s, 1H), 5.59 (m, 2H), 5.42 (s, 2H), 5.39 (s, 1H), 5.24-5.16 (m, 1H), 4.50 (m, 1H), 4.19 ~ 4.08 (m, 2H), 2.22-2.00 (m, 12H), 1.05 (d, 6H, J = 7.4 Hz)

IR (KBr, cm ^-1 ): 1770, 1645, 1605, 1430, 1380

Elemental Analysis for C ₃₃ H ₃₆ O ₁₄

Calculated (%): C 60.36; H 5.53; O 34.11

Found (%): C 60.39; H 5.64; O 33.97

Compound 80

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.72 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.44 (s, 2H), 5.41 (s, 1H), 5.23-5.14 (m, 1H), 5.00 (m, 1H), 4.21 ~ 4.09 (m, 2H), 2.23-1.26 (m, 21H), 0.96 (d, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 1750, 1640, 1600, 1445, 1380

Elemental Analysis for C ₃₇ H ₄₂ O ₁₄

Calculated (%): C 62.53; H 5.96; O 31.51

Found (%): C 62.63; H 5.85; O 31.52

Compound 81

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.73 (d, 1H, J = 8.8 Hz), 7.59-7.18 (m, 5H), 6.87 (d, 1H, J = 8.8 Hz), 6.74 ( s, 1H), 6.44 (dd, 1H, J = 17.5 Hz, J = 9.4 Hz), 6.00 (s, 1H), 5.50 (m, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.23 ~ 5.15 (m, 1H), 4.20 ~ 4.10 (m, 2H), 4.13 (dd, 1H, J = 17.6Hz, J = 2.0Hz), 3.91 (dd, 1H, J = 9.4Hz, J = 1.9Hz ), 2.22-2.00 (m, 12H)

IR (KBr, cm ^-1 ): 1765, 1640, 1600, 1435, 1375

Elemental Analysis for C ₃₂ H ₃₂ O ₁₄

Calculated Value (%): C 60.00, H 5.04, O 34.96

Found (%): C 59.97; H 5.10; O 34.93

Compound 82

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.70 (d, 1H, J = 8.8 Hz), 7.58-7.20 (m, 5H), 6.86 (d, 1H, J = 8.8 Hz), 6.78 ( s, 1H), 6.00 (s, 1H), 5.50 (m, 2H), 5.43 (s, 2H), 5.41 (s, 1H), 5.34 (m, 2H), 5.21-5.13 (m, 1H), 4.26 (t, 2H, J = 6.2Hz), 4.20 ~ 4.12 (m, 2H), 2.30 ~ 1.96 (m, 16H), 0.98 (t, 3H, J = 7.2Hz)

IR (KBr, cm ^-1 ): 1760, 1650, 1610, 1440, 1370

Elemental Analysis for C ₃₆ H ₄₀ O ₁₄

Calculated (%): C 62.06; H 5.79; O 32.15

Found (%): C 62.03; H 5.88; O 32.09

Compound 83

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.72 (d, 1H, J = 8.8 Hz), 7.60-7.20 (m, 5H), 6.85 (d, 1H, J = 8.8 Hz), 6.76 ( s, 1H), 6.02 (s, 1H), 5.50 (m, 2H), 5.44 (s, 2H), 5.41 (s, 1H), 5.34 (m, 1H), 5.20-5.13 (m, 2H), 4.19 ~ 4.11 (m, 2H), 4.12 (d, 2H, J = 8.6 Hz), 2.20-1.98 (m, 16H), 1.68 (s, 6H), 1.58 (s, 3H)

IR (KBr, cm ^-1 ): 1765, 1645, 1600, 1440, 1370

Elemental Analysis for C ₄₀ H ₄₆ O ₁₄

Calculated (%): C 63.99; H 6.18; O 29.83

Found (%): C 63.88; H 6.23; O 29.89

Compound 84

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.69 (d, 1H, J = 8.8 Hz), 7.55 to 7.15 (m, 25H), 6.73 (d, 1H, J = 8.8 Hz), 6.81 ( s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.40 (s, 1H), 5.36 (s, 2H), 5.22-5.14 (m, 9H), 4.49 (t, 2H, J = 6.8 Hz), 4.18-4.10 (m, 2H), 180-1.20 (m, 12H), 0.89 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 1650, 1610, 1435, 1380

Elemental Analysis for C ₅₈ H ₆₂ O ₁₀

Calculated (%): C 75.79; H 6.80; O 17.41

Found (%): C 75.87; H 6.74; O 17.39

Compound 85

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.68 (d, 1H, J = 8.8 Hz), 7.60-7.15 (m, 30H), 6.90 (d, 1H, J = 8.8 Hz), 6.80 ( s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.46 (s, 2H), 5.41 (s, 1H), 5.22-5.15 (m, 11H), 4.18-4.09 (m, 2H)

IR (KBr, cm ^-1 ): 1640, 1600, 1445, 1370

Elemental Analysis for C ₅₇ H ₅₂ O ₁₀

Calculated (%): C 76.32; H 5.84; O 17.84

Found (%): C 76.56; H 5.79; O 17.65

Compound 86

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.25 (bs, 1H), 7.60 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.22 (bs, 1H), 4.96 (d, 1H, J = 7.6 Hz), 4.90 (bs, 1H), 4.68 (bs, 1H), 4.55 (bs, 1H), 4.50 (t, 2H, J = 6.6 Hz), 3.64-3.24 (m , 6H), 1.75-1.20 (m, 4H), 0.88 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3400, 2940, 2900, 2840, 1670, 1635, 1610, 1250

Elemental Analysis for C ₁₉ H ₂₄ O ₁₀

Calculated (%): C 55.33; H 5.87; O 38.80

Found (%): C 55.30; H 5.93; O 38.77

Compound 87

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.35 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.08-6.98 (m, 2H), 5.20 (bs, 1H), 4.97 (d, 1H, J = 7.6 Hz), 4.90 (bs, 1H), 4.68 (bs, 1H), 4.54 (bs, 1H), 4.49 (t, 2H, J = 6.6 Hz), 3.65-3.24 (m , 6H), 1.81-1.20 (m, 8H), 0.90 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3400, 2960, 2900, 2840, 1675, 1630, 1610, 1250

Elemental Analysis for C ₂₁ H ₂₈ O ₁₀

Calculated (%): C 57.26; H 6.41; O 36.33

Found (%): C 57.40; H 6.40; O 36.20

Compound 88

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.10 (bs, 1H), 7.62 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.20 (bs, 1H), 4.98 (d, 1H, J = 7.6 Hz), 4.90 (bs, 1H), 4.65 (bs, 1H), 4.52 (bs, 1H), 4.52 (t, 2H, J = 6.6 Hz), 3.64-3.24 (m , 6H), 180-1.15 (m, 12H), 0.89 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3450, 2940, 2910, 2850, 1675, 1630, 1610, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 58.96; H 6.89; O 34.15

Found (%): C 58.90; H 6.93; O 34.17

Compound 89

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.15 (bs, 1H), 7.60 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.20 (bs, 1H), 4.95 (d, 1H, J = 7.6 Hz), 4.90 (bs, 1H), 4.68 (bs, 1H), 4.52 (bs, 1H), 4.49 (t, 2H, J = 6.6 Hz), 3.64-3.24 (m , 6H), 1.81-1.20 (m, 16H), 0.92 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3400, 2940, 2900, 2850, 1670, 1630, 1610, 1250

Elemental Analysis for C ₂₅ H ₃₆ O ₁₀

Calculated (%): C 60.47; H 7.31; O 32.22

Found (%): C 60.40; H 7.40; O 32.20

Compound 90

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.20 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.01 (m, 2H), 5.24 (bs, 1H), 4.91 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.65 (bs, 1H), 4.50 (bs, 1H), 4.49 (t, 2H, J = 6.6 Hz), 3.65-3.25 (m , 6H), 1.79-1.20 (m, 20H), 0.88 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2945, 2920: 2850, 1675, 1630, 1600, 1250

Elemental Analysis for C ₂₇ H ₄₀ O ₁₀

Calculated (%): C 61.81; H 7.69; O 30.50

Found (%): C 61.75; H 7.50; O 30.75

Compound 91

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.30 (bs, 1H), 7.59 (d, 1H, J = 9.6 Hz), 7.12-7.02 (m, 2H), 5.20 (bs, 1H), 4.93 (d, 1H, J = 7.6 Hz), 4.85 (bs, 1H), 4.67 (bs, 1H), 4.49 (m, 2H), 3.65-3.25 (m, 6H), 1.04 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 3400, 2960, 2930, 2850, 1690, 1635, 1610, 1250

Elemental Analysis for C ₁₈ H ₂₂ O ₁₀

Calculated (%): C 54.27; H 5.57; O 40.16

Found (%): C 54.17; H 5.57; O 40.26

Compound 92

¹ H-NMR (CDCl ₃ , δ -TMS): 10.40 (bs, 1H), 7.60 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.20 (bs, 1H), 5.03 ( m, 1H), 4.90 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.66 (bs, 1H), 4.55 (bs, 1H), 3.63-3.23 (m, 6H), 2.19-1.13 (m, 9H), 0.95 (d, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 3340, 2970, 2920, 2850, 1680, 1635, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₈ O ₁₀

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.35; H 6.30; O 35.35

Compound 93

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.85 (bs, 1H), 7.59 (d, 1H, J = 9.6 Hz), 7.09-6.99 (m, 2H), 6.45 (dd, 1H, J = 17.5 Hz, J = 9.5 Hz), 5.20 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.68 (bs, 1H), 4.52 (bs, 1H), 4.15 (dd, 1H, J = 17.5 Hz, J = 2.0 Hz), 3.93 (dd, 1H, J = 9.5 Hz, J = 2.0 Hz), 3.64-3.24 (m, 6H).

IR (KBr, cm ^-1 ): 3360, 2950, 2900, 2850, 1670, 1630, 1610, 1250

Elemental Analysis for C ₁₇ H ₁₈ O ₁₀

Calculated (%): C 53.40; H 4.75; O 41.85

Found (%); C 53.51, H 4.78; O 41.71

Compound 94

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.73 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.11-7.01 (m, 2H), 5.50 (m, 1H), 5.35 (m, 1H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.91 (bs, 1H), 4.67 (bs, 1H), 4.50 (bs, 1H), 4.27 (t , 2H, J = 6.2Hz), 3.65 ~ 3.25 (m, 6H), 2.33 ~ 1.97 (m, 4H), 0.99 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3340, 2950, 2920, 1710, 1630, 1605, 1260

Elemental Analysis for C ₂₁ H ₂₆ O ₁₀

Calculated (%): C 57.53; H 5.98; O 36.49

Found (%): C 57.67; H 5.95; O 36.38

Compound 95

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.29 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.09-7.00 (m, 2H), 5.40 (m, 1H), 5.21 (bs, 1H), 5.11 (m, 1H), 4.94 (d, 1H, J = 7.6 Hz), 4.86 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.15 (d , 2H, J = 8.5Hz), 3.66 ~ 3.26 (m, 6H), 2.01 (m, 4H), 1.67 (s, 6H), 1.64 (s, 3H)

IR (KBr, cm ^-1 ): 3350, 2950, 2915, 1700, 1660, 1605, 1260

Elemental Analysis for C ₂₅ H ₃₂ O ₁₀

Calculated (%): C 60.96; H 6.55; O 32.49

Found (%): C 60.93; H 6.62; O 32.45

Compound 96

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.13 (bs, 1H), 7.60 (d, 1H, J = 9.6 Hz), 7.34 (m, 5H), 7.10-7.05 (m, 2H), 5.28 (s, 2H), 5.19 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.90 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 3.65-3.24 (m, 6H)

IR (KBr, cm ^-1 ): 3330, 3300, 2930, 2840, 1700, 1620, 1260

Elemental Analysis for C ₂₂ H ₂₂ O ₁₀

Calculated (%): C 59.19; H 4.97; O 35.84

Found (%): C 59.28; H 4.85; O 35.87

Compound 97

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.55 (s, 1H), 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6 Hz), 5.04 (t, 1H, J = 9.8 Hz), 4.40-4.10 (m, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm ^-1 ): 3320, 2950, 1750, 1620, 1370, 1240

Elemental Analysis for C ₂₅ H ₂₆ O ₁₅

Calculated (%): C 53.00; H 4.59; O 42.41

Found (%): C 52.95; H 4.55; O 42.50

Compound 98

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t , 1H, J = 9.8Hz), 4.40 ~ 4.10 (m, 3H), 4.15 (s, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₂₆ H ₂₈ O ₁₅

Calculated (%): C 53.79; H 4.83; O 41.38

Found (%): C 53.85; H 4.79; O 41.36

Compound 99

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t , 1H, J = 9.8Hz), 4.46 (t, 2H, J = 6.0Hz), 4.40 ~ 4.10 (m, 3H), 2.25 (q, 2H, J = 7.2Hz), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 180 to 1.70 (m, 2H), 1.55 to 1.40 (m, 2H), 1.05 (t, 3H, J = 7.2 Hz), 0.93 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2950, 2920, 2850, 1730, 1640, 1610, 1260

Elemental Analysis for C ₃₀ H ₃₆ O ₁₅

Calculated (%): C 56.60; H 5.66; O 37.74

Found (%): C 56.55; H 5.79; O 37.66

Compound 100

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.35-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.30 ~ 5.18 (m, 8H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.46 (t, 2H, J = 6.0Hz), 4.40 ~ 4.10 (m, 3H), 2.25 ( q, 2H, J = 7.2 Hz), 1.95-1.40 (m, 16H), 1.07 (t, 3H, J = 7.2 Hz), 0.93 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2920, 2850, 1725, 1640, 1610, 1250

Elemental Analysis for C ₅₆ H ₆₄ O ₁₁

Calculated (%): C 73.68; H 7.02; O 19.30

Found (%): C 73.65; H 7.05; O 19.30

Compound 101

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.40-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.30 ~ 5.18 (m, 8H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.46 (t, 2H, J = 6.0Hz), 4.40 ~ 4.10 (m, 3H), 2.05 ~ 1.40 (m, 20H), 1.05 (t, 3H, J = 7.4 Hz), 0.93 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2920, 2850, 1700, 1640, 1610, 1250

Elemental Analysis for C ₅₈ H ₆₈ O ₁₁

Calculated (%): C 74.04; H 7.23; O 18.73

Found (%): C 74.08; H 7.35; O 18.57

Compound 102

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.40-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.30 ~ 5.18 (m, 8H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.10 (m, 4H), 2.25 (s, 3H), 1.05 (d, J = 7.5 Hz, 6H)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1610, 1250

Elemental Analysis for C ₄₈ H ₄₈ O ₁₁

Calculated (%): C 72.00; H 6.00; O 22.00

Found (%): C 71.95; H 5.96; O 22.09

Compound 103

¹ H-NMR (CDCl ₃ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz), 5.74 (d, 1H, J = 7.6 Hz), 5.41 (t, 1H, J = 9.4 Hz), 5.13 (dd, 1H, J = 7.6 Hz, J = 9.6 Hz), 5.04 (t, 1H , J = 9.8 Hz), 4.99 (m, 1H), 4.40-4.10 (m, 3H), 2.34 (s, 3H), 2.20-1.25 (m, 9H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.98 (d, 3H, J = 6.4 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₃₂ H ₃₈ O ₁₅

Calculated (%): C 58.00; H 5.74; O 36.26

Found (%): C 57.95; H 5.79; O 36.26

Compound 104

¹ H-NMR (DMSO-d ₆ , δ- TMS): 77.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz), 6.45 (dd, 1H, J = 17 Hz, J = 9.5 Hz), 5.74 (d, 1H, J = 7.6 Hz), 5.41 (t, 1H, J = 9.4 Hz), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.10 (m, 4H), 3.95 (dd, 1H, J = 9.5Hz, J = 2.0Hz) , 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1605, 1250

Elemental Analysis for C ₂₇ H ₂₈ O ₁₅

Calculated (%): C 54.73; H 4.73; O 40.54

Found (%): C 54.85; H 4.69; O 40.46

Compound 105

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz) 5.34 (m, 2H), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6 Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40-4.10 (m, 5H), 2.34 (s, 3H), 2.30-1.95 (m, 4H), 2.04 (s, 3H), 2.03 (s , 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.97 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1720, 1610, 1250

Elemental Analysis for C ₃₁ H ₃₆ O ₁₅

Calculated (%): C 57.41; H 5.56; O 37.03

Found (%): C 57.45; H 5.59; O 36.96

Compound 106

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz), 5.74 (d, 1H, J = 7.6 Hz), 5.41 (t, 1H, J = 9.4 Hz) 5.13 (dd, 1H, J = 7.6 Hz, J = 9.6 Hz), 5.11 (m, 2H), 5.04 (t, 1H, J = 9.8Hz), 4.40-4.22 (m, 3H), 4.10 (d, 2H, J = 8.5Hz), 2.30 (m, 4H), 2.05 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.85 (m, 2H), 1.67 (s, 6H), 1.60 (s, 3H), 1.55 (m, 2H), 1.05 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1620, 1260

Elemental Analysis for C ₃₇ H ₄₆ O ₁₅

Calculated (%): C 60.82; H 6.30; O 32.88

Found (%): C 60.85; H 6.35; O 32.80

Compound 107

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.35-7.15 (m, 25H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.20 ~ 5.35 (m, 10H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.15 (m, 3H), 2.30 (t, 2H, J = 6.8Hz), 1.55 ( m, 2H), 1.05 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1705, 1620, 1260

Elemental Analysis for C ₅₄ H ₅₂ O ₁₁

Calculated (%): C 73.97, H 5.94; O 20.09

Found (%): C 73.95; H 5.96; O 20.09

Compound 108

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.45 (s, 1H), 9.19 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 3.75-3.10 (m, 6H)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1600, 1260

Elemental Analysis for C ₁₅ H ₁₆ O ₁₀

Calculated (%): C 50.56; H 4.53; O 44.91

Found (%): C 50.55; H 4.49; O 44.96

Compound 109

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.35 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.23 (s, 3H), 3.75-3.10 (m, 6H)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental Analysis for C ₁₆ H ₁₈ O ₁₀

Calculated (%): C 51.89; H 4.90; O 43.21

Found (%): C 51.85; H 4.79; O 43.36

Compound 110

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.25 (t, 2H, J = 6.2 Hz), 3.75-3.10 (m , 6H), 180 ~ 1.20 (m, 4H), 0.85 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1700, 1640, 1610, 1260

Elemental Analysis for C ₁₉ H ₂₄ O ₁₀

Calculated (%): C 55.33; H 5.87; O 38.80

Found (%): C 55.25; H 5.89; O 38.86

Compound 111

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.10 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.95 (a, 1H, J = 7.2 Hz), 4.59 (bs, 1H), 4.40 (t, 2H, J = 6.4 Hz), 3.75-3.10 (m , 6H), 1.80 ~ 1.60 (m, 2H), 1.52 ~ 1.15 (m, 14H), 0.85 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 3350, 2920, 2850, 1700, 1640, 1610, 1250

Elemental Analysis for C ₂₅ H ₃₆ O ₁₀

Calculated Value (%): C 60.47, H 7.31, O 32.22

Found (%): C 60.35; H 7.45; O 32.20

Compound 112

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.15 (bs, 1H), 7.60 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J = 7.2 Hz), 4.59 (bs, 1H), 4.25 (t, 2H, J = 6.4 Hz), 3.75-3.10 (m , 6H), 180 ~ 1.60 (m, 2H), 1.52 ~ 1.12 (m, 18H), 0.85 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 3350, 2920, 2850, 1700, 1640, 1610, 1250

Elemental Analysis for C ₂₇ H ₄₀ O ₁₀

Calculated (%): C 61.81; H 7.69; O 30.50

Found (%): C 61.75; H 7.45; O 30.80

Compound 113

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.35 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.45 (m, 1H), 3.75-3.10 (m, 6H), 1.05 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental Analysis for C ₁₈ H ₂₂ O ₁₀

Calculated (%): C 54.27; H 5.57; O 40.16

Found (%): C 54.18; H 5.69; O 40.13

Compound 114

¹ H-NMR (CDCl ₃ , δ -TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.35 (bs, 1H), 5.11 ( bs, 1H), 5.05 (bs, 1H), 5.00 (m, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 3.75-3.10 (m, 6H), 2.02-1.20 (m, 9H), 0.98 (d, 3H, J = 6.5 Hz)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₈ O ₁₀

Calculated Value (%): C 58.40, H 6.24, O 35.36

Found (%): C 58.45; H 6.29; O 35.26

Compound 115

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 6.55 (dd, 1H, J = 17.5 Hz, J = 9.5 Hz, 5.35 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.16 (dd, 1H, J = 17.5Hz, J = 2.0Hz), 3.95 (dd, 1H, J = 9.5Hz, J = 2.0Hz), 3.75 ~ 3.10 (m, 6H)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental Analysis for C ₁₇ H ₁₈ O ₁₀

Calculated (%): C 53.40; H 4.75; O 41.85

Found (%): C 53.55; H 4.79; O 41.66

Compound 116

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.55 (m, 1H), 5.34 (m, 2H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.27 (t, 2H, J = 6.2 Hz ), 3.75 ~ 3.10 (m, 6H), 2.30 ~ 1.95 (m, 4H), 0.97 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 1700, 1640, 1605 1260

Elemental Analysis for C ₂₁ H ₂₆ O ₁₀

Calculated (%): C 57.53; H 5.98; O 36.49

Found (%): C 57.75; H 5.79, O 36.46

Compound 117

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.10-7.00 (m, 2H), 5.40 (m, 1H), 5.37 (bs, 1H), 5.11 (m, 2H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 4.12 (d, 2H, J = 8.5 Hz ), 3.75-3.10 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 1700, 1640, 1605, 1260

Elemental Analysis for C ₂₅ H ₃₂ O ₁₀

Calculated (%): C 60.96; H 6.55; O 32.49

Found (%): C 60.85; H 6.75; O 32.40

Compound 118

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.35-7.20 (m, 5H), 7.10-7.00 (m, 2H ), 5.37 (bs, 1H), 5.25 (s, 2H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J = 6.8 Hz), 4.59 (bs, 1H), 3.75 ~ 3.10 (m, 6H)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1620, 1260

Elemental Analysis for C ₂₂ H ₂₂ O ₁₀

Calculated (%): C 59.19; H 4.97; O 35.84

Found (%): C 59.25; H 4.79; O 35.96

Compound 119

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.55 (s, 1H), 7.77 (d, 1H, J = 8.8 Hz), 7.30-7.15 (m, 2H), 5.94 (s, 1H), 5.45 to 5.35 (m, 2H), 5.13 (t, 1H, J = 10.0 Hz), 4.20 to 3.90 (m, 3H), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H) , 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm ^-1 ): 3320, 2950, 1750, 1620, 1370, 1240

Elemental Analysis for C ₂₅ H ₂₆ O ₁₅

Calculated (%): C 53.00; H 4.59; O 42.41

Found (%): C 52.95; H 4.55; O 42.50

Compound 120

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.30-7.15 (m, 2H), 5.94 (s, 1H), 5.45-5.35 (m, 2H ), 5.13 (t, 1H, J = 10 Hz), 4.20-3.90 (m, 3H), 4.15 (s, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₂₆ H ₂₈ O ₁₅

Calculated (%): C 53.79; H 4.83; O 41.38

Found (%): C 53.85; H 4.79; O 41.36

Compound 121

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.30-7.15 (m, 22H), 5.94 (s, 1H), 5.45-5.35 (m, 2H ), 5.25 (m, 8H), 5.13 (t, 1H, J = 10.0 Hz), 4.20-3.90 (m, 3H), 4.46 (t, 2H, J = 6.0 Hz), 2.25 (q, 2H, J = 7.2 Hz), 1.80 to 1,40 (m, 12H), 1.05 (t, 3H, J = 7.2 Hz), 0.95 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2950, 2920, 2850, 1730, 1640, 1610, 1260

Elemental Analysis for C ₅₄ H ₆₀ O ₁₁

Calculated (%): C 73.30; H 6.78; O 19.92

Found (%): C 73.35; H 6.80; O 19.85

Compound 122:

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.35-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.94 (s, 1H), 5.45 ~ 5.35 (m, 2H), 5.30 ~ 5.18 (m, 8H), 5.13 (t, 1H, J = 10.0Hz ), 4.20-3.90 (m, 3H), 4.46 (t, 2H, J = 6.0 Hz), 2.23 (q, 2H, J = 7.0 Hz), 1.95-1.40 (m, 16H), 1.07 (t, 3H, J = 7.0 Hz), 0.93 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2920, 2850, 1725, 1640, 1610, 1250

Elemental Analysis for C ₅₆ H ₆₄ O ₁₁

Calculated (%): C 73.68; H 7.02; O 19.30

Found (%): C 73.65; H 7.05; O 19.30

Compound 123

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.40-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.30 ~ 5.18 (m, 8H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.46 (t, 2H, J = 6.0Hz), 4.40 ~ 4.10 (m, 3H), 2.34 ( s, 3H), 2.26 (q, 2H, J = 7.0Hz), 2.05-1.40 (m, 20H), 1.05 (t, 3H, J = 7.0Hz), 0.93 (t, 3H, J = 6.8Hz)

IR (KBr, cm ^-1 ): 2920, 2850, 1700, 1640, 1610, 1250

Elemental Analysis for C ₅₈ H ₆₈ O ₁₁

Calculated (%): C 74.04; H 7.23; O 18.73

Found (%): C 74.08; H 7.35; O 18.57

Compound 124

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.40-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.18-5.30 (m, 8H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.10 (m, 4H), 2.25 (s, 3H), 1.05 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1610, 1250

Elemental Analysis for C ₄₈ H ₄₈ O ₁₁

Calculated (%): C 72.00; H 6.00; O 22.00

Found (%): C 71.95; H 5.96; O 22.09

Compound 125

¹ H-NMR (CDCl ₃ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.30-7.15 (m, 2H), 5.94 (s, 1H), 5.45-5.35 (m, 2H), 5.13 (t, 1H, J = 10.0 Hz), 5.05 (m, 1H), 4.20-3.90 (m, 3H), 2.34 (s, 3H), 2.20-1.25 (m, 9H), 2.04 (s, 3H) , 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.95 (d, 3H, J = 6.6 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₃₂ H ₃₈ O ₁₅

Calculated (%): C 58.00; H 5.74; O 36.26

Found (%): C 58.04; H 5.79; O 36.17

Compound 126

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.30-7.15 (m, 2H), 5.94 (s, 1H), 6.45 (dd, 1H, J = 17.5 Hz, J = 9.5 Hz); 5.45-5.35 (m, 2H), 5.13 (t, 1H, J = 10.0 Hz), 4.20-3.90 (m, 5H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H) , 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₂₇ H ₂₈ O ₁₅

Calculated (%): C 54.73; H 4.73; O 40.54

Found (%): C 54.75; H 4.79; O 40.46

Compound 127

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz), 5.74 (d, 1H, J = 7.6 Hz), 5.41 (t, 1H, J = 9.4 Hz), 5.34 (m, 2H), 5.13 (dd, 1H, 2 = 7.6 Hz, J = 9.6 Hz), 5.04 (t, 1H, J = 9.8 Hz), 4.40 to 4.10 (m, 5H), 2.34 (s, 3H), 2.30 to 1.95 (m, 4H), 2.04 (s, 3H), 2.03 ( s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.97 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1610, 1250

Elemental Analysis for C ₃₁ H ₃₆ O ₁₅

Calculated (%): C 57.41; H 5.56; O 37.03

Found (%): C 57.45; H 5.59; O 36.96

Compound 128

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz), 5.74 (d, 1H, J = 7.6 Hz), 5.41 (t, 1H, J = 9.4 Hz) 5.13 (dd, 1H, J = 7.6 Hz, J = 9.6 Hz), 5.11 (m, 2H), 5.04 (t, 1H, J = 9.8Hz), 4.40-4.22 (m, 3H), 4.12 (d, 2H, J = 8.5Hz), 2.30 (m, 4H), 2.05 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.67 (s, 6H), 1.60 (s, 3H), 1.55 (m, 2H), 1.05 (t, 3H, J = 6.9 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1620, 1260

Elemental Analysis for C ₃₇ H ₄₆ O ₁₅

Calculated (%): C 60.82; H 6.30; O 32.88

Found (%): C 60.85; H 6.35; O 32.80

Compound 129

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.35-7.15 (m, 25H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.35-5.20 (m, 10H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.15 (m, 3H), 2.25 (t, 2H, J = 6.9Hz), 1.56 ( m, 2H), 1.04 (t, 3H, J = 6.9 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1705, 1620, 1260

Elemental Analysis for C ₅₄ H ₅₂ O ₁₁

Calculated (%): C 73.97; H 5.94; O 20.09

Found (%): C 73.98; H 5.96; O 20.06

Compound 130

¹ H-NMR (DMSO-d ₆ , δ -TMS): 10.15 (s, 1H), 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2 Hz, J = 9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.85 ( s, 1H), 3.75-3.20 (m, 6H)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₁₆ H ₁₆ O ₁₀

Calculated (%): C 50.56; H 4.53; O 44.91

Found (%): C 50.52; H 4.55; O 44.93

Compound 131

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.20 (s, 3H), 3.85 ( s, IH), 3.75-3.20 (m, 6H)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₁₆ H ₁₈ O ₁₀

Calculated (%): C 51.89; H 4.90; O 43.21

Found (%): C 51.83; H 4.85; O 43.32

Compound 132

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.20 (bs, 2H), 7.55 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J = 6.4 Hz), 3.85 (s, 1H), 3.75-3.20 (m, 6H), 1.80-1.30 (m, 12H), 0.87 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₃ H ₃₂ O ₁₀

Calculated (%): C 58.96; H 6.89; O 34.15

Found (%): C 58.95; H 6.85; O 34.20

Compound 133

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.42 (t, 2H, J = 6.4 Hz), 3.85 (s, 1H), 3.75-3.20 (m, 6H), 1.80-1.25 (m, 16H), 0.85 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₅ H ₃₆ O ₁₀

Calculated (%): C 60.47; H 7.31; O 32.22

Found (%): C 60.35; H 7.45; O 32.20

Compound 134

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.42 (t, 2H, J = 6.4 Hz), 3.85 (s, 1H), 3.75-3.20 (m, 6H), 1.90-1.25 (m, 20H), 0.85 (t, 3H, J = 7.2 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₇ H ₄₀ O ₁₀

Calculated (%): C 61.81; H 7.69; O 30.50

Found (%): C 61.75; H 7.45; O 30.80

Compound 135

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.28 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.45 (m, 1H), 3.85 ( s, 1H), 3.75-3.10 (m, 6H), 1.05 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₁₈ H ₂₂ O ₁₀

Calculated (%): C 54.27; H 5.57; O 40.16

Found (%): C 54.10; H 5.65; O 40.25

Compound 136

¹ H-NMR (CDCl ₃ , δ- TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.99 (m, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.75 ~ 3.20 ( m, 6H), 2.20-1.25 (m, 9H), 0.95 (d, 3H, J = 6.7 Hz)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₈ O ₁₀

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.43; H 6.35; O 35.22

Compound 137

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 6.45 (dd, 1H, J = 17.5Hz, J = 9.5Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H) , 4.77 (bs, 1H), 4.15 (dd, 1H, J = 17.5 Hz, J = 2.0 Hz), 3.95 (dd, 1H, J = 9.5 Hz, J = 2.0 Hz), 3.85 (s, 1H), 3.75 ~ 3.20 (m, 6H)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₁₇ H ₁₈ O ₁₀

Calculated (% :): C 53.40; H 4.75; O 41.85

Found (%): C 53.33; H 4.80; O 41.87

Compound 138

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.55 (m, 1H), 5.34 (m, 2H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.27 ( t, 2H, J = 6.2Hz), 3.85 (s, 1H), 3.75 ~ 3.20 (m, 6H), 2.30 ~ 1.95 (m, 4H), 0.97 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₁ H ₂₆ O ₁₀

Calculated (%): C 57.53; H 5.98; O 36.49

Found (%): C 57.57; H 5.85; O 36.58

Compound 139

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2Hz, J = 9.0Hz), 5.47 (s, 1H), 5.41 (m, 1H), 5.13 (m, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 ( bs, 1H), 4.12 (d, 2H, J = 8.5 Hz), 3.85 (s, 1H), 3.75-3.20 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s , 3H)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C25H ₃₂ O ₁₀

Calculated (%): C 60.96; H 6.55; O 32.49

Found (%): C 60.89; H 6.65; O 32.36

Compound 140

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.35 (m, 5H), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2 Hz, J = 9.0 Hz), 5.47 (s, 1H), 5.23 (s, 2H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 ( bs, 1H), 3.85 (s, 1H), 3.75-3.20 (m, 6H)

IR (KBr, cm ^-1 ): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₂ O ₁₀

Calculated (%): C 59.19; H 4.97; O 35.84

Found (%): C 59.25; H 4.79; O 35.96

Compound 141

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.25 (bs, 1H), 7.77 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.05 (dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 2.4Hz), 5.30-5.20 (m, 2H), 4.52 (t, 1H, J = 6.6Hz), 4.11 (d, 2H, J = 6.0Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 ( s, 3 H)

IR (KBr, cm ^-1 ): 2950, 1750, 1620, 1370, 1240

Elemental Analysis for C ₂₅ H ₂₆ O ₁₅

Calculated (%): C 53.00; H 4.59; O 42.41

Found (%): C 52.95; H 4.55; O 42.50

Compound 142

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.05 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 2.4H 5.30-5.20 (m, 2H), 4.52 (t, 1H, J = 6.6Hz), 4.25 (s, 3H), 4.11 (d, 2H, J = 6.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₂₆ H ₂₈ O ₁₅

Calculated (%): C 53.79; H 4.83; O 41.38

Found (%): C 53.85; H 4.79; O 41.36

Compound 143

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.35-7.20 (m, 20H), 7.11 (d, 1H, J = 2.4 Hz), 7.05 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 2.4Hz), 5.30 ~ 5.20 (m, 2H), 5.30 ~ 5.18 (m, 8H), 4.52 (t, 1H, J = 6.6 Hz), 4.46 (t, 2H, J = 6.0 Hz), 4.11 (d, 2H, J = 6.0 Hz), 1.95-1.40 (m, 16H ), 2.30 (q, 2H, J = 7.1 Hz), 1.10 (t, 3H, J = 7.1 Hz), 0.93 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2920, 2850, 1725, 1640, 1610, 1250

Elemental Analysis for C ₅₆ H ₆₄ O ₁₁

Calculated (%): C 73.68; H 7.02, O 19.30

Found (%): C 73.65; H 7.05; O 19.30

Compound 144

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.35-7.20 (m, 20H), 7.11 (d, 1H, J = 2.4 Hz), 7.05 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 2.4Hz), 5.30 ~ 5.20 (m, 2H), 5.30 ~ 5.18 (m, 8H), 4.52 (t, 1H, J = 6.6 Hz), 4.38 (t, 2H, J = 6.0 Hz), 4.11 (d, 2H, J = 6.0 Hz), 2.25 (q, 2H, J = 7.2 Hz), 1.95-1.40 (m, 20H), 1.10 (t, 3H, J = 7.2 Hz), 0.93 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2920, 2850, 1700, 1640, 1610, 1250

Elemental Analysis for C ₅₈ H ₆₈ O ₁₁

Calculated (%): C 74.04; H 7.23; O 18.73

Found (%): C 74.08; H 7.35; O 18.57

Compound 145

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.40-7.20 (m, 20H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.30 ~ 5.18 (m, 8H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.10 (m, 4H), 2.25 (s, 3H), 1.05 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1610, 1250

Elemental Analysis for C ₄₈ H ₄₈ O ₁₁

Calculated (%): C 72.00, H 6.00; O 22.00

Found (%): C 71.95; H 5.96; O 22.09

Compound 146

¹ H-NMR (CDCl ₃ , δ -TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.05 (dd, 1H, J = 2.4 Hz, J = 8.8 Hz), 5.66 (d, 1H, J = 7.2 Hz), 5.38 (d, 1H, J = 2.4 Hz), 5.30-5.20 (m, 2H), 5.02 (m, 1H), 4.52 (t, 1H, J = 6.6 Hz), 4.11 (d, 2H, J = 6.0 Hz), 2.34 (s, 3H), 2.25-1.24 (m, 9H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 ( s, 3H), 1.96 (s, 3H), 0.97 (d, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₃₂ H ₃₈ O ₁₅

Calculated (%): C 58.00; H 5.74; O 36.26

Found (%): C 57.95; H 5.79; O 36.26

Compound 147

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.11 (d, 1H, J = 2.4 Hz), 7.05 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 6.44 (dd, 1H, J = 17.5Hz, J = 9.5Hz), 5.66 (d, 1H, J = 7.2Hz), 5.38 (d, 1H, J = 2.4Hz), 5.30 ~ 5.20 (m, 2H), 4.52 (t, 1H, J = 6.6 Hz), 4.20 (dd, 1H, J = 17.5 Hz, J = 2.0 Hz), 4.11 (d, 2H, J = 6.0 Hz), 3.96 (dd , 1H, J = 9.5Hz, J = 2.0Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H)

IR (KBr, cm ^-1 ): 2950, 2850, 1725, 1610, 1250

Elemental Analysis for C ₂₇ H ₂₈ O ₁₅

Calculated (%): C 54.73; H 4.73; O 40.54

Found (%): C 54.85; H 4.79; O 110.36

Compound 148

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.77 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz) 5.34 (m, 2H), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6 Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40-4.10 (m, 5H), 2.34 (s, 3H), 2.30-1.95 (m, 4H), 2.04 (s, 3H), 2.03 (s , 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.97 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1610, 1250

Elemental Analysis for C ₃₁ H ₃₅ O ₁₅

Calculated (%): C 57.41; H 5.56; O 37.03

Found (%): C 57.45; H 5.59; O 36.96

Compound 149

¹ H-NMR (DMSO-d ₆ , δ- TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.06 (dd, 1H, J = 2.4 Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.13 (dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.11 (m , 2H), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.22 (m, 3H), 4.12 (d, 2H, J = 8.5Hz), 2.35 (m, 4H), 2.05 (m, 2H) , 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.67 (s, 6H), 1.60 (s, 3H), 1.55 (m, 2H), 1.00 (t, 3H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1735, 1620, 1260

Elemental Analysis for C ₃₇ H ₄₆ O ₁₅

Calculated (%): C 60.82; H 6.30; O 32.88

Found (%): C 60.85; H 6.35; O 32.80

Compound 150

¹ H-NMR (DMSO-d ₆ , δ -TMS): 7.65 (d, 1H, J = 8.8 Hz), 7.35-7.15 (m, 25H), 7.12 (d, 1H, J = 2.4 Hz), 7.06 ( dd, 1H, J = 2.4Hz, J = 8.8Hz), 5.74 (d, 1H, J = 7.6Hz), 5.41 (t, 1H, J = 9.4Hz), 5.35-5.20 (m, 10H), 5.13 ( dd, 1H, J = 7.6Hz, J = 9.6Hz), 5.04 (t, 1H, J = 9.8Hz), 4.40 ~ 4.15 (m, 3H), 2.25 (t, 2H, J = 7.0Hz), 1.55 ( m, 2H), 1.00 (t, 3H, J = 7.0 Hz)

IR (KBr, cm ^-1 ): 2950, 2850, 1705, 1620, 1260

Elemental Analysis for C ₅₄ H ₅₂ O ₁₁

Calculated (%): C 73.97; H 5.94; O 20.09

Found (%): C 73.94; H 5.96; O 20.10

Compound 151

¹ H-NMR (DMSO-d ₆ , δ- TMS): 10.24 (bs, 1H), 9.17 (bs, 1H), 7.61 (d, 1H, J = 8.8 Hz), 7.12 (d, 1H, J = 2.4 Hz), 7.07 (dd, 1H, J = 2.2 Hz, J = 9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.85 ( s, 1H), 3.75-3.20 (m, 6H)

IR (KBr, cm ^-1 ): 3400, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₁₅ H ₁₆ O ₁₀

Calculated (%): C 5 O.56; H 4.53; O 44.91

Found (%): C 50.52; H 4.55; O 44.93

Compound 152

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.35 (m, 5H), 7.10-7.00 (m, 2H), 5.28 (s, 2H), 5.21 (bs, 1H), 4.92 (d, IH, 1 = 7.6 Hz), 4.88 (bs, IH), 4.67 (bs, 1H), 4.52 (bs, 1H), 3.65-3.25 (m, 6H)

IR (KBr, cm ^-1 ): 3330, 3300, 2950, 2850, 1700, 1620, 1260

Elemental Analysis for C ₂₂ H ₂₂ O ₁₀

Calculated (%): C 59.19; H 4.97; O 35.84

Found (%): C 59.33; H 4.89; O 35.78

Compound 153

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.23 (s, 3H), 3.65-3.25 (m, 6H)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₁₆ H ₁₈ O ₁₀

Calculated (%): C 51.89; H 4.90; O 43.21

Found (%): C 51.85, H 4.78; O 43.37

Compound 154

¹ H-NMR (DMSO-d ₆ , δ -TMS): 9.16 (bs, 1H), 7.61 (d, IH, 1 = 9.6 Hz), 7.10-7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.47 (t, 2H, J = 6.6 Hz), 3.65-3.25 (m , 6H), 1.80 ~ 1.70 (m, 2H), 1.60 ~ 1.20 (m, 14H), 0.90 (t, 3H, J = 7.2Hz)

IR (KBr, cm ^-1 ): 3400, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₂₅ H ₃₆ O ₁₀

Calculated (%): C 60.47; H 7.31; O 32.22

Found (%): C 60.45; H 7.40; O 32.15

Compound 155

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.10 (bs, 1H), 7.60 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.65 (bs, 1H), 4.52 (bs, 1H), 4.47 (t, 2H, J = 6.6 Hz), 3.65-3.25 (m , 6H), 180 ~ 1.70 (m, 2H), 1.60 ~ 1.20 (m, 18H), 0.90 (t, 3H, J = 7.2Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₂₇ H ₄₀ O ₁₀

Calculated (%): C 61.81; H 7.69; O 30.50

Found (%): C 61.75; H 7.45; O 30.80

Compound 156

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.07 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.50 (m, 2H), 3.65-3.25 (m, 6H), 1.05 (d, 6H, J = 7.5 Hz)

IR (KBr, cm ^-1 ): 3400, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₁₈ H ₂₂ O ₁₀

Calculated Value (%): C 54.27, H 5.57, O 40.16

Found (%): C 54.07; H 5.67; O 40.26

Compound 157

¹ H-NMR (CDCl 3, δ-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.21 (bs, 1H), 5.00 (m , 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 3.65-3.25 (m, 6H), 2.20-1.14 ( m, 9H), 0.96 (d, 2H, J = 6.8 Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₂₂ H ₂₈ O ₁₀

Calculated (%): C 58.40; H 6.24; O 35.36

Found (%): C 58.25; H 6.38; 0 35.37

Compound 158

¹ H-NMR (OMSO-d ₆ , δ -TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 6.45 (dd, 1H, J = 17.5 Hz, J = 9.5 Hz), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H, 4.52 (bs, 1H), 4.15 (dd, 1H, J = 17.5Hz, J = 2.0Hz), 3.96 (dd, 1H, J = 9.5Hz, T = 2.0Hz), 3.65 ~ 3.25 (m, 6H)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental Analysis for C ₁₇ H ₁₈ O ₁₀

Calculated (%): C 53.40; H 4.75; O 41.85

Found (%): C 53.45; H 4.78; O 41.77

Compound i59

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.55 (m, 1H), 5.34 (m, 1H), 5.21 (bs, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.27 (t , 2H, J = 6.2Hz), 3.65 ~ 3.25 (m, 6H), 2.30 ~ 1.95 (m, 4H), 0.97 (t, 3H, J = 7.0Hz)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 1700, 1640, 1605, 1260

Elemental Analysis for C ₂₁ H ₂₆ O ₁₀

Calculated (%): C 57.53; H 5.98; O 36.49

Found (%): C 57.77; H 5.85; O 36.38

Compound 160

¹ H-NMR (DMSO-d ₆ , δ- TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J = 9.6 Hz), 7.10-7.00 (m, 2H), 5.40 (m, 1H), 5.21 (bs, 1H), 5.11 (m, 1H), 4.92 (d, 1H, J = 7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.15 (d , 2H, J = 8.5Hz), 3.65 ~ 3.25 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm ^-1 ): 3350, 2950, 2920, 1700, 1640, 1605, 1260

Elemental Analysis for C ₂₅ H ₃₂ O ₁₀

Calculated (%): C 60.96; H 6.55; O 32.49

Found (%): C 60.83; H 6.62; O 32.55

Test Example

Acute Toxicity Test in Mice

We conducted this test to confirm the safety of the compounds of the invention. The acute toxicity test method is described next.

Method: 7-glycosyloxybenzopyran derivatives (compounds 3, 8, 9, 11, 15, 16, 18 to 23, 35, 37 to 47, 61 to 72, 75, 86 to 96, 99, 108 to 118, 130-140, 145, 151-160, forcibly orally administered to male ICR mice (20-25 g body weight, 5 mice per group (1) group) at doses of 1000 mg / kg and 2000 mg / kg using esophageal mediators do. After administration, animals are placed in cages for 7 days to observe general symptoms and count the number of dead animals. The lethal dose (LD ₅₀ : mg / kg) is extrapolated from deaths 7 days after administration.

As a result, it is evident that the LD ₅₀ of all 7-glycosyloxybenzopyran derivatives is at least 2000 mg / kg and therefore the compounds of the invention are extremely low in toxicity.

Test Example 2

Effects on Homologous Passive Skin Anaphylaxis (PCA) Responses in Rats

We perform these pharmacological tests by the PCA response, a well-known screening test for antiallergic agents, to demonstrate that compounds of the invention have antiallergic activity. This experimental animal model produces an immediate allergic reaction, ie an antigen-antibody response. Next, the pharmacological test method will be described.

Methods: 0.05 ml of antiserum against dinitrophenylated ascaris (DNP-As) is administered intracutaneously in two places on the shaved dorsal skin of male Wister rats (9 weeks old). After 48 hours, the animal is orally administered to the animal at a dose of 50 mg / kg of 7-glycosyloxybenzopyran derivative (test compound) suspended in 0.5% sodium carboxymethyl cellulose (CMCNa). One hour after administration of the test compound, anaphylaxis is induced by injection of saline (1 ml) in which 5 mg of Evans Blue and 1 mg of trinitrophenylated ascaris (TNP-As) are injected into the tail vein of the animal. Thirty minutes after anaphylaxis is induced, the animal is anesthetized with ether, bleeded to death, and the dorsal skin removed. Extravasated pigments are described in Katayama et al., Microbiol. Immunol., Vol. 22, p 89-101, 1978]. As an excipient control group, only 0.5% CMCNa solution is administered orally, and the trianilast suspended in 0.5% CMCNa as a positive control group is administered orally to animals in the same manner as the test compound group at a dose of 100 mg / kg. Percent inhibition of PCA response was calculated according to Equation 1 and the results are shown in Table 2. Each experimental group consists of 5 rats.

(Equation 1)

In the above formula,

A is the amount of pigment in the excipient control group,

B is the pigment amount of a test compound group or a positive control group.

TABLE 2

Table 2 (continued)

As shown in Table 2, all compounds of the present invention demonstrate that the antiallergic activity is equal to or better than tranilast. As a result of these examples it is clear that the compounds of the invention are useful antiallergic agents for immediate allergic diseases.

Comparative Test Example 1

Effects on Homologous Passive Skin Anaphylaxis (PCA) Responses in Rats

The antiallergic activity of the compounds of the present invention is compared with the activity of similar compounds disclosed in the patent for PCA reaction (W092 / 13852). This pharmacological test is performed according to the method described in Test Example 2. Comparative compounds are shown in Table 3 and the results are shown in Table 4.

TABLE 3

Table 4

From the results of Test Example 2 and the comparative test example, it is clear that the antiallergic activity of the compound of the present invention 7-glycoside is higher than that of the comparative compound.

Test Example 3

Effect on Contact Dermatitis Caused by Picryl Chloride in Mice

We demonstrate that this pharmacological test is carried out by well-known experimental contact dermatitis models to demonstrate that the compounds of the present invention inhibit delayed oversensitization. This experimental animal model, which is a typical delayed oversensitization model, is primarily caused by a cellular immune response. Immunology, Vol. 15, p. 405-416, 1968]. Delayed-type hypersensitivity is inhibited by steroids, but cannot be affected by known antiallergic agents. The following describes the pharmacological test method.

Methods: Mice shaved on the abdomen skin the day before were immunized with 0.1 ml of acetone containing 7 mg of picryl chloride on the abdomen skin. Seven days after immunization, ear thickness is measured with a dial thickness gauge and then challenged by applying 5 μl of a 1% picryl chloride olive oil solution to both sides of the skin of the mouse's left ear. After 24 hours of challenge, the left ear thickness is measured again and the percent thickness increase is calculated according to equation (2). Compounds of the invention (test compounds) suspended in 0.5% CMCNa are forced orally administered at a dose of 50 mg / kg 1 hour before challenge and 16 hours after challenge. As an excipient control group, only 0.5% CMCNa solution is administered orally, and as a positive control group, the steroid hormones prednisolone and tranilast are administered orally at doses of 10 mg / kg and 100 mg / kg, respectively. The percent inhibition against increasing thickness of the excipient control group was calculated according to Equations 2 and 3 and the results are shown in Table 5.

(Equation 2)

% Growth = (A-B) / Bx100

In the above formula,

A is the ear thickness after 24 hours of challenge,

B is the ear thickness before the challenge.

(Equation 3)

% Growth = (C-D) / Cx100

In the above formula,

C is the percentage increase in excipient control group,

D is the percentage increase in test compound group or positive control group.

Table 5

Table 5 (continued)

Test compounds are observed to effectively inhibit ear dilatation by 40-65% compared to the excipient control group. Many of the compounds of the present invention are equivalent to or better than prednisolone (inhibition rate: 63.7%). In contrast, tranilast, widely used in allergic diseases, does not inhibit delayed hypersensitivity. These results clearly show that the compounds of the present invention have a large inhibitory activity against delayed type hypersensitivity. Thus, the compounds of the present invention are very useful antiallergic agents.

Test Example 4

Effects on Guinea Pigs' Experimental Asthma Model

Asthma is a typical allergic disease, and we perform this pharmacological test by well-known experimental asthma models of guinea pigs to confirm that the compounds of the present invention inhibit asthma. Next, the pharmacological test method is described below.

Methods: Male, Hartley guinea pigs were immunized with three intraperitoneal injections of saline (1 ml) containing 5 mg of egg white albumin (OVA) at weekly intervals. Finally, two weeks after immunization, challenge with 1% OVA- saline solution inhaled for 1 minute in the animal, and then inhalation of the animal's airway resistance, followed by PULMOS-1 [Medical Interface Project Station Inc.) for 30 minutes. The compound of the invention (test compound) suspended in 0.5% CMCNa is administered orally at a dose of 50 mg / kg. As a positive control group, disodium chromoglycate (DSCG), a well known antiallergic agent in saline, is injected at a dose of 20 mg / kg into the vein of an animal. Only the 0.5% CMCNa solution is administered orally as an excipient control group. Inhibition of airway resistance (%) of the excipient control group was calculated according to Equation 5 and the results are shown in Table 6. Each experimental group consists of 5 guinea pigs.

(Equation 5)

In the above formula,

A is the maximum airway resistance of the excipient control group,

B is the maximum airway resistance of the test compound group or positive control group.

Table 6

Table 6 (continued)

As shown in Table 6, the orally administered compounds of the invention inhibit the airway resistance increase by 40-80%. Thus, the compounds of the present invention have very high activity in treating asthma.

Formulation Example 1

(5% powder)

Compound 43 50mg

Lactose 950mg

1000 mg

Crystals of compound 43 are ground in the mortar and then the mixture is ground with a pestle to thoroughly mix with lactose to give a 5% powder.

Formulation Example 2

(5% powder)

Compound 154 50mg

Lactose 950mg

1000 mg

The procedure of Formulation Example 1 is repeated to yield 5% powder.

Formulation Example 3

(10% granules)

Compound 62 300 mg

Lactose 200mg

Starch 670mg

Gelatin 30mg

3000 mg

Compound 62 is mixed with the same amount of starch and ground in mortar. It is further mixed with lactose and the remaining amount of starch. Separately, 30 mg of gelatin is mixed with 1 ml of purified water, heated to dissolve, cooled, and mixed with 1 ml of ethanol while stirring to prepare a gelatin solution. The mixture prepared above is then mixed with a gelatin solution and the resulting mixture is kneaded, granulated and dried to give granules.

Formulation Example 4

(10% granules)

Compound 132 300mg

Lactose 2000mg

Starch 670mg

30 mg gelaton

3,000 mg

The procedure of Formulation Example 3 is repeated to yield 10% granules.

Formulation Example 5

(5mg tablets)

Compound 21 5mg

Lactose 62mg

Starch 30mg

Talc 2mg

Magnesium Stearate 1mg

100 mg / tablet

A tablet containing 5 mg each of Compound 21 was prepared using 20 times more than the composition. That is, 100 mg of compound 21, crystalline form, is ground in a mortar and then mixed with lactose and starch. The formulation so prepared is mixed with 10% starch paste, the mixture is kneaded and then granulated. After drying, the resulting granules are mixed with talc and magnesium stearate and compressed into conventional means.

Formulation Example 6

(5mg tablets)

Compound 110 5mg

Lactose 62mg

Starch 30mg

Talc 2mg

Magnesium Stearate 1mg

100 mg / tablet

Formulation Example 5 was repeated to yield 5 mg tablets.

Formulation Example 7

(20mg tablet)

Compound 22 20mg

6% Hydroxypropylcellulose / Lactose 75mg

Stearate / Talc 2mg

Potato starch 3mg

100 mg / tablet

A tablet containing 20 mg of each active ingredient is prepared using 10 times more than the composition. That is, 6 g of hydroxypropyl cellulose is dissolved in an appropriate amount of ethanol, mixed with 94 g of lactose, and then kneaded. After some drying, the mixture is passed through mesh 60 and so graded granules are used as 6% hydroxypropyl cellulose / lactose. Separately, magnesium stearate and talc are mixed in a ratio of 1: 4 and used as stearate / talc. Thereafter, compound 22, 6% hydroxypropylcellulose / lactose, stearate / talc and potato starch are thoroughly mixed and compressed in a conventional manner.

Formulation Example 8

(20mg tablet)

Compound 87 20mg

6% Hydroxypropylcellulose / Lactose 75mg

Stearate / Talc 2mg

Potato starch 3mg

100 mg / tablet

Formulation Example 7 was repeated to yield 20 mg tablets.

Formulation Example 9

(25 mg tablets)

Compound 68 25mg

Lactose 122mg

50 mg of carboxyethyl starch

Talc 2mg

Magnesium Stearate 1mg

200 mg / starch

10 times more than the compound is used to induce a tablet containing 25 mg of each active ingredient. That is, 250 mg of compound 68 in crystalline form is ground in a mortar and then thoroughly mixed with lactose. Appropriate amount of purified water is added to carboxyethyl starch and then it is added to the mixture, the resulting mixture is kneaded and then granulated. After drying, the granules thus prepared are mixed with talc and magnesium stearate and compressed into conventional means.

Formulation Example 10

(25 mg tablets)

Compound 153 25mg

Lactose 122mg

50 mg of carboxyethyl starch

Talc 2mg

Magnesium Stearate 1mg

200 mg / tablet

Formulation Example 9 was repeated to yield 25 mg tablets.

Formulation Example 11

(10mg capsule)

Compound 38 300mg

Lactose 2000mg

Starch 670mg

Gelatin 30mg

3000 mg

Granules are prepared according to the procedure described in Formulation Example 3 and filled into capsules at 100 mg.

Formulation Example 12

(10mg capsule)

Compound 116 300 mg

Lactose 2000mg

Starch 670mg

Gelatin 30mg

3000 mg

Formulation Example 11 was repeated to yield 100 mg capsules.

Formulation Example 13

10mg (0.1% injection solution)

Polyethylene Glycol 400 3ml

Polysorbate 80 0.01ml

Distilled water rest for injection

10 ml

Compound 3 is dissolved in a mixed solution of polyethylene glycol 400 and polysorbate 80, the total volume of the resulting solution is adjusted to 10 ml by gradually adding distilled water for injection, and the solution thus prepared is filled into an ampoule aseptically. .

Formulation Example 14

(0.1% injection solution) Compound 18 10mg

Polyethylene Glycol 400 3ml

Polysorbate 80 0.01ml

Distilled water rest for injection

10 ml

Formulation Example 13 was repeated to obtain 0.1% injection.

As such, it is clear to provide novel 7-glycosyloxybenzopyran derivatives useful in pharmaceutical formulations according to the present invention. It also provides excellent antiallergic agents that are low toxicity and useful for treating or preventing immediate and delayed allergic diseases, particularly excellent antiallergic agents that are very effective against delayed allergies that cannot be effectively treated with prior art antiallergic agents.

Although the present invention has been described in detail with the creation of specific aspects thereof, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

Claims (31)

7-glycosyloxybenzopyran derivatives of formula (I) and physiologically acceptable salts thereof. In the above formula, R ₁ is a hydrogen atom, acyl group, alkyl group, cycloalkyl group, alkenyl group or aralkyl group, R ₂ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group, R ₃ is a glycosyl group wherein the hydroxyl group is protected or unprotected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups. The 7-glycosyloxybenzopyran derivative according to claim 1, wherein R ₁ is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group, and R ₂ is a hydrogen atom or an aralkyl group Physiologically acceptable salts thereof. The 7-glycosyloxybenzopyran derivative and physiologically acceptable according to claim 1, wherein R ₁ is a hydrogen atom or an acyl group and R ₃ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group. Salts thereof. The 7-glycosyloxybenzopyran derivative according to claim 1, wherein R ₁ is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group, and R ₂ is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group; Physiologically acceptable salts thereof. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1 to 3, wherein the acyl group is an alkanoyl group and the aralkyl group is a benzyl group. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1, 2 and 4, wherein R ₁ is an alkyl group having 1 to 12 carbon atoms. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1, 2 and 4, wherein R ₁ is a cycloalkyl group having 5 to 8 carbon atoms. The 7-glycosyloxybenzopyran derivative and the physiologically acceptable salt thereof according to any one of claims 1, 2 and 4, wherein R ₁ is an alkenyl group having 2 to 10 carbon atoms. The 7-glycosyloxybenzopyran derivative according to claim 4, wherein R ₁ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, and R ₂ is a hydrogen atom. And physiologically acceptable salts thereof. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1, 3 and 4, wherein R ₂ is an alkyl group having 1 to 12 carbon atoms. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1, 3 and 4, wherein R ₂ is a cycloalkyl group having 5 to 8 carbon atoms. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1, 3 and 4, wherein R ₂ is an alkenyl group having 2 to 10 carbon atoms. The 7-glycosyloxybenzopyran derivative according to claim 4, wherein R ₁ is a hydrogen atom, R ₂ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms. And physiologically acceptable salts thereof. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1 to 4, 9 and 13, wherein R ₃ is a glucosyl group. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1 to 4, 9 and 13, wherein R ₃ is a mannosyl group. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1 to 4, 9 and 13, wherein R ₃ is a galactosyl group. The 7-glycosyloxy benzopyran derivative and physiologically acceptable salt thereof according to any one of claims 1 to 4, 9 and 13, wherein R ₃ is an unprotected glycosyl group. The 7-glycosyloxybenzopyran derivative and physiologically acceptable according to any one of claims 1 to 4, 9 and 13, wherein R ₃ is a glycosyl group protected with an acyl or aralkyl group. Salts thereof. An antiallergic pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) or a physiologically acceptable salt thereof according to claim 1 and a pharmaceutically acceptable carrier. The anti-allergic pharmaceutical composition according to claim 19, wherein R ₁ is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group, and R ₂ is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group. The anti-allergic pharmaceutical composition according to claim 20, wherein R ₁ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms. The anti-allergic pharmaceutical composition according to claim 20, wherein R ₁ is a hydrogen atom and R ₂ is an alkyl group, a cycloalkyl group or an alkenyl group. The anti-allergic pharmaceutical composition according to claim 20, wherein R ₁ is an alkyl group, a cycloalkyl group or an alkenyl group and R ₂ is a hydrogen atom. The anti-allergic pharmaceutical composition according to claim 23, wherein R ₁ is an alkyl group having 1 to 12 carbon atoms. The anti-allergic pharmaceutical composition according to claim 23, wherein R ₁ is a cycloalkyl group having 5 to 8 carbon atoms. The anti-allergic pharmaceutical composition according to claim 23, wherein R ₁ is an alkenyl group having 2 to 10 carbon atoms. 27. An antiallergic pharmaceutical composition according to any one of claims 19 to 26 wherein R ₃ is a glucosyl group. 27. The antiallergic pharmaceutical composition of any of claims 19-26, wherein R ₃ is a mannosyl group. 27. An antiallergic pharmaceutical composition according to any one of claims 19 to 26, wherein R ₃ is a galactosyl group. 27. An antiallergic pharmaceutical composition according to any one of claims 19 to 26 wherein R ₃ is an unprotected glucosyl group. 27. An antiallergic pharmaceutical composition according to any of claims 19 to 26, wherein R ₃ is a glycosyl group protected with an acyl or aralkyl group.